Odorless Thioacetalization Reagent 2‐[1,3]Dithian‐2‐Ylidene‐3‐Oxo‐Butanamide and Its Chemoselectivity

References

• Kocienski , P. J. 1994 . Protecting Groups Stuttgart : Thieme .
   Google Scholar
• Greene , T. W. and Wuts , P. G.M. 1999 . Protective Groups in Organic Synthesis , 3rd Ed. New York : John Wiley and Sons .
   Google Scholar
• Corey , E. J. and Seebach , D. 1966 . Phenylthiomethyllithium and Bis(phenylthio)methyllithium . J. Org. Chem. , 31 : 4097
   Web of Science ®Google Scholar
• Groebel , B.‐T. and Seebach , D. 1977 . Umpolung of the reactivity of carbonyl compounds through sulfur‐containing reagents . Synthesis , 6 : 357
   Google Scholar
• Seebach , D. 1979 . Methods of reactivity umpolung . Angew. Chem. Int. Ed. Engl. , 18 : 239
   Web of Science ®Google Scholar
• Rychnovsky , S. D. 1995 . Oxo polyene macrolide antibiotics . Chem. Rev. , 95 : 2021
   Web of Science ®Google Scholar
• Smith , A. B. III. , Condon , S. M. and McCauley , J. A. 1998 . Total synthesis of immunosuppressants: unified strategies exploiting dithiane couplings and σ‐bond olefin constructions . Acc. Chem. Res. , 31 : 35
   Web of Science ®Google Scholar
• Breit , B. 1998 . Dithioacetals as an entry to titanium‐alkylidene chemistry: a new and efficient carbonyl olefination . Angew. Chem. Int. Ed. Engl. , 37 ( 4 ) : 453
   PubMed Web of Science ®Google Scholar
• Smith , A. B. III. , Pitram , S. M. , Gaunt , M. J. and Kozmin , S. A. 2002 . Dithiane additions to vinyl epoxides: steric control over the SN2 and SN2′ manifolds . J. Am. Chem. Soc. , 124 : 14516
   PubMed Web of Science ®Google Scholar
• Corey , E. J. and Shimoji , K. 1983 . Magnesium and zinc‐catalyzed thioketalization . Tetrahedron Lett. , 24 : 169
   Web of Science ®Google Scholar
• Kumar , V. and Dev , S. 1983 . Titanium tetrachloride, an efficient and convenient reagent for thioacetalization . Tetrahedron Lett. , 24 : 1289
   Web of Science ®Google Scholar
• Tani , H. , Masumoto , K. , Inamasu , T. and Suzuki , H. 1991 . Tellurium tetrachloride as a mild and efficient catalyst for dithioacetalization . Tetrahedron Lett. , 32 : 2039
   Web of Science ®Google Scholar
• Page , P. C.B. , Prodger , J. C. and Westwood , D. 1993 . Diastereoselectivity in the addition of grignard reagents to ketones controlled by the 1,3‐dithiane 1‐oxide asymmetric building block . Tetrahedron , 49 : 10355
   Web of Science ®Google Scholar
• Kumar , P. , Reddy , R. S. , Singh , A. P. and Pandey , B. 1993 . An expeditious synthesis of dithioacetals using zeolites . Synthesis , 67 ( 1 )
   Google Scholar
• Bellesia , F. , Boni , M. , Ghelf , F. and Pagnoni , U. M. 1993 . α‐Chloromer‐captals from α‐chloroacetals and thiols . Tetrahedron , 49 : 199
   Web of Science ®Google Scholar
• Anand , R. V. , Saravanan , P. and Singh , V. K. 1999 . Solvent free thioacetalization of carbonyl compounds catalyzed by Cu(OTf)2‐SiO2 . Synlett , 4 : 415
   Google Scholar
• Tietze , L. F. , Weigand , B. and Wulff , C. 2000 . A mild and efficient method for the preparation of 1,3‐dithianes from aldehydes and ketones . Synthesis , 69 ( 1 )
   Google Scholar
• Garlaschelli , L. and Vidari , G. 1990 . Anhydrous lanthanum trichloride, a mild and convenient reagent for thioacetalization . Tetrahedron Lett. , 31 : 5815
   Web of Science ®Google Scholar
• Patney , H. K. 1991 . A rapid mild and efficient method of thioacetalization using anhydrous iron(III) chloride dispersed on silicagel . Tetrahedron Lett. , 32 : 2259
   Web of Science ®Google Scholar
• Kumar , P. , Reddy , R. S. , Singh , A. P. and Pandey , B. 1992 . H‐Y zeolite an efficient catalyst for thioacetalization . Tetrahedron Lett. , 33 : 825
   Web of Science ®Google Scholar
• Saraswathy , V. G. and Sankararaman , S. 1994 . Chemoselective protection of aldehydes as dithioacetals in lithium perchlorate‐diethyl ether medium. Evidence for the formation of oxocarbenium ion intermediate from acetals . J. Org. Chem. , 59 : 4665
   Web of Science ®Google Scholar
• Firouzabadi , H. , Iranpoor , N. and Hazarkhani , H. 2001 . Iodine catalyzes efficient and chemoselective thioacetalization of carbonyl functions, transthioacetalization of O,O‐ and S,O‐acetals and acylals . J. Org. Chem. , 66 : 7527
   PubMed Web of Science ®Google Scholar
• Muthusamy , S. , Babu , S. A. and Gunanathan , C. 2001 . Indium(III) chloride as an efficient, convenient catalyst for thioacetalization and its chemoselectivity . Tetrahedron Lett. , 42 : 359
   Web of Science ®Google Scholar
• Samajdar , S. , Basu , M. K. , Becker , F. F. and Banik , B. K. 2001 . A new molecular iodine‐catalyzed thioketalization of carbonyl compounds: selectivity and scope . Tetrahedron Lett. , 42 : 4425
   Web of Science ®Google Scholar
• Kamal , A. and Chouhan , G. 2002 . Scandium triflate as a recyclable catalyst for chemoselective thioacetalization . Tetrahedron Lett. , 43 : 1347
   Web of Science ®Google Scholar
• Firouzabadi , H. , Iranpoor , N. and Amani , K. 2002 . Synthesis of arylglycines by reaction of diethyl N‐boc‐iminomalonate with organomagnesium reagents . Synthesis , 1 : 59
   Google Scholar
• Kamal , A. and Chouhan , G. 2003 . Chemoselective thioacetalization and transthioacetalization of carbonyl compounds catalyzed by immobilized scandium(III) triflate in ionic liquids . Tetrahedron Lett. , 44 : 3337
   Web of Science ®Google Scholar
• Node , M. , Kumura , K. , Nishide , K. , Ohsugi , S. and Miyamoto , T. 2001 . Odorless substitutes for foul‐smelling thiols: syntheses and applications . Tetradedron Lett. , 42 : 9207
   Web of Science ®Google Scholar
• Nishide , K. , Miyamoto , T. , Kumura , K. , Ohsugi , S. I. and Node , M. 2002 . Synthetic equivalents of benzenethiol and benzyl mercaptan having faint smell: odor reducing effect of trialkylsilyl group . Tetrahedron Lett. , 43 : 8569
   Web of Science ®Google Scholar
• Nishide , K. , Ohsugi , S. I. , Fudesaka , M. , Kodama , S. and Node , M. 2002 . New odorless protocols for the Swern and Corey–Kim oxidations . Tetrahedron Lett. , 43 : 5177
   Web of Science ®Google Scholar
• Bertini , V. , Lucchesini , F. , Pocci , M. and De Munno , A. 1998 . 1,3‐Dithiane polymers for the supported synthesis of ketones . Tetrahedron Lett. , 39 : 9263
   Web of Science ®Google Scholar
• Bertini , V. , Lucchesini , F. , Pocci , M. and De Munno , A. 2000 . Polymeric reagents with propane‐1,3‐dithiol functions and their precursors for supported organic syntheses . J. Org. Chem. , 65 : 4839
   PubMed Web of Science ®Google Scholar
• Bertini , V. , Pocci , M. , Lucchesini , F. , Alfei , S. and De Munno , A. 2003 . Polystyrene resins containing 1,3‐propanedithiol functions for solid‐phase organic syntheses . Synlett. , 6 : 864
   Google Scholar
• Limura , S. , Manabe , K. and Kobayashi , S. 2003 . Hydrophobic polymer‐supported catalyst for organic reactions in water: acid‐catalyzed hydrolysis of thioesters and transprotection of thiols . Org. Lett. , 5 ( 2 ) : 101
   PubMed Web of Science ®Google Scholar
• Liu , Q. and Zhao , B. 1992 . Synthesis of 1,1‐dialkylthio‐1,3,5‐hexatrienes with α‐oxoketene dithioacetals . Chin. Chem. Lett. , 3 ( 4 ) : 241
   Google Scholar
• Liu , Q. , Dong , D. , Yang , Z. , Jing , F. and Xiao , Y. 1993 . The chemistry of α‐oxoketene cyclic dithioacetals(VI)—studies on the dehydration of adducts of β, β‐1,3‐propylene‐dithio‐α, β‐unsaturated arylketones with allyl grignard reagents . Chem. J. Chin. Univ. , 14 ( 3 ) : 353
   Google Scholar
• Liu , Q. , Wang , Z. , Zhang , S. and Yang , Z. 1994 . Studies on the reactivity of cydoaromatization reaction via α‐oxoketene dithioacetals . Chin. Chem. Lett. , 5 ( 7 ) : 577
   Google Scholar
• Wang , M. , Xu , X. , Liu , Q. , Xiong , L. , Yang , B. and Gao , L. 2002 . Iododecarboxylation of α‐carboxylate, α‐cinnamoyl ketene cyclicdithioacetals . Syn. Commun. , 32 : 3437
   Web of Science ®Google Scholar
• Zhao , Y. , Liu , Q. , Sun , R. , Zhang , Q. and Xu , X. 2004 . Reaction of arylglyoxals with electron‐rich benzenes and π‐excessive heterocycles. Facile synthesis of heteroaryl α‐acyloins . Syn. Commun. , 34 : 463
   Web of Science ®Google Scholar
• Liu , Y. , Dong , D. , Liu , Q. , Qi , Y. and Wang , Z. 2004 . A novel and facile synthesis of dienals and substituted 2H‐pyrans via the Vilsmeier reaction of α‐oxo‐ketenedithioacetals . Org. Biomol. Chem. , 2 : 28
   PubMed Web of Science ®Google Scholar
• Liu , Q. , Che , G. , Yu , H. , Liu , Y. , Zhang , J. , Zhang , Q. and Dong , D. 2003 . The first nonthiolic, odorless 1,3‐propanedithiol equivalent and its application in thioacetalization . J. Org. Chem. , 68 : 9148
   PubMed Web of Science ®Google Scholar
• Yu , H. , Liu , Q. , Yin , Y. , Fang , Q. , Zhang , J. and Dong , D. 2004 . α,α‐Diacetyl cyclic ketene dithioacetals: odorless and efficient dithiol equivalents in thioacetalization reactions . Synlett. , 6 : 999
   Google Scholar
• Dieter , R. K. 1986 . α‐Oxo ketene dithioacetals and related compounds: versatile three‐carbon synthons . Tetrahedron , 42 : 3029
   Web of Science ®Google Scholar
• Junjappa , H. , Ila , H. and Asokan , C. V. 1990 . α‐Oxoketene‐S,S‐, N,S‐ and N,N‐Acetals: versatile intermediates in organic synthesis . Tetrahedron , 46 : 5423
   Web of Science ®Google Scholar
• Kolb , M. 1990 . Ketene dithioacetals in organic synthesis: recent developments . Synthesis , 3 : 171
   Google Scholar
• Choi , E. B. , Youn , I. K. and Pak , C. S. 1988 . Preparation of protected β‐keto aldehydes from β‐keto esters via selective reduction of acyl(alkoxycarbonyl)ketene dithioacetals . Synthesis , : 792
   Web of Science ®Google Scholar
• Mellor , J. M. , Schofield , S. R. and Korn , S. R. 1997 . Routes to building blocks for heterocyclic synthesis by reduction of ketene dithioacetals . Tetrahedron , 53 ( 50 ) : 17151
   Web of Science ®Google Scholar
• Zhang , S. , Liu , Q. , Zhu , Z. , Zhang , C. and Huang , H. 1994 . Studies on the basic assisted decomposition of α, α‐dioxo(ester) ketene dithioacetals . Chem. J. Chin. Univ. , 15 ( 8 ) : 1155
   Google Scholar
• Zhao , Y. , Liu , Q. , Sun , R. and Chi , Y. 2004 . Preparation of α‐nitroketene dithioacetals . Chem. J. Chin. Univ. , 25 ( 2 ) : 2
   Google Scholar