Stereoselective Synthesis of Allylic Amines by One-Pot Tandem Reaction of Acetylenic Sulfone, Grignard Reagent, and N-Tosylimine

REFERENCES

• (a) Nishina , N. ; Yamamoto , Y. Gold-catalyzed intermolecular hydroamination of allenes with arylamines and resulting high chirality transfer . Angew. Chem. Int. Ed. 2006 , 45 , 3314 – 3317 ; (b) García-Egido , E. ; Fernández , I. ; Muñoz , L. Convenient synthesis of oxazolidinones and oxazinones from allyl and homoallyl amines under mild conditions . Synth. Commun. 2006 , 36 , 3029 – 3042 ; (c) Hodgson , D. M. ; Fleming , M. J. ; Stanway , S. J. One-carbon homologation of N-sulfonylaziridines to allylic amines using dimethylsulfonium methylide . Org. Lett. 2005 , 7 , 3295 – 3298 ; (d) Ichikawa , Y. ; Ito , T. ; Nishiyama , T. ; Isobe , M. Stereoselective allyl amine synthesis via enantioselective addition of diethylzinc and sigmatropic rearrangement: Synthesis of lentiginosine . Synlett 2003 , 1034 – 1036 ; (e) Johannsen , M. ; Jørgensen , K. A. Allylic Amination . Chem. Rev. 1998 , 98 , 1689 – 1708 .
   Google Scholar
• (a) Matsui , K. ; Takizawa , S. ; Sasai , H. Bifunctional organocatalysts for enantioselective aza-morita-baylis-hillman reaction. J. Am. Chem. Soc. 2005, 127, 3680–3681; (b) Katritzky , A. R. ; Yao , J. C. ; Qi , M. Palladium-catalyzed reaction of N-allylbenzotriazoles with amines: A novel method for the preparation of allylamines. J. Org. Chem. 1998, 63, 5232–5234; (c) Kondo , T. ; Nakai , H. ; Goto , T. Synthesis of cytosinine, the nucleoside component of antibiotic blasticidin S. Tetrahedron 1973, 29, 1801–1806.
   Google Scholar
• Chen , G. ; Sasaki , M. ; Yudin , A. K. Facile preparation of allyl amines and pyrazoles by hydrazinolysis of 2-ketoaziridines . Tetrahedron Lett. 2006 , 47 , 255 – 259 and references therein .
   Web of Science ®Google Scholar
• (a) Concellón , J. M. ; Suárez , J. R. ; Solar , V. Synthesis of enantiopure allylamines by reductive alkylation of amino epoxides with organolithium reagents . Org. Lett. 2006 , 8 , 349 – 351 ; (b) Singh , V. ; Pathak , R. ; Kanojiya , S. ; Batra , S. A reinvestigation into the reaction of NH4OAc with acetyl derivatives of baylis-hillman adducts: Formation of tertiary and secondary allyl amines instead of primary allyl amines . Synlett 2005 , 2465 – 2468 ; (c) Yamasaki , S. ; Fujii , K. ; Wada , R. ; Kanai , M. ; Shibasaki , M. A General catalytic allylation using allyltrimethoxysilane . J. Am. Chem. Soc. 2002 , 124 , 6536 – 6537 ; (d) Evans , P. A. ; Robinson , J. E. ; Nelson , J. D. Enantiospecific synthesis of allylamines via the regioselective rhodium-catalyzed allylic amination reaction . J. Am. Chem. Soc. 1999 , 121 , 6761 – 6762 ; (e) Marson, C. M.; Hobson, A. D. In Comprehensive Organic Functional Group Transformations; A. R. Katrizky, O. Meth-Cohn, C. W. Rees (Eds.); Pergamon: Oxford, 1995, vol. 2, p. 297.
   Google Scholar
• (a) Back , T. G. ; Rankic , D. A. ; Sorbetti , J. M. ; Wulff , J. E. Morita-baylis-hillman reaction and cyclization of 1-(p-toluenesulfonyl)-1,3-butadiene with aldimines . Org. Lett. 2005 , 7 , 2377 – 2379 ; (b) Dieter, R. K.; Dieter, J. W.; Alexander, C. W.; Bhinderwala, N. S. Efficient synthesis of allylic amines from α-aminoalkyl cuprates and enol triflates. J. Org. Chem. 1996, 61, 2930–2931.
   Google Scholar
• (a) Zhou , C. X. ; Larock , R. C. Regio- and stereoselective route to tetrasubstituted olefins by the palladium-catalyzed three-component coupling of aryl iodides, internal alkynes, and arylboronic acids . J. Org. Chem. 2005 , 70 , 3765 – 3777 ; (b) Itami, K.; Mineno, M.; Muraoka, N.; Yoshida, J. Sequential assembly strategy for tetrasubstituted olefin synthesis using vinyl 2-pyrimidyl sulfide as a platform. J. Am. Chem. Soc. 2004, 126, 11778–11779; (c) Stüdemann, T.; Knochel, P. New nickel-catalyzed carbozincation of alkynes: A short synthesis of (Z)-tamoxifen. Angew. Chem., Int. Ed. Engl. 1997, 36, 93–95.
   Google Scholar
• (a) Shirakawa , E. ; Yamagami , T. ; Kimura , T. ; Yamaguchi , S. ; Hayashi , T. Arylmagnesiation of alkynes catalyzed cooperatively by iron and copper complexes . J. Am. Chem. Soc. 2005 , 127 , 17164 – 17165 ; (b) Maezaki, N.; Sawamoto, H.; Suzuki, T.; Yoshigami, R.; Tanaka, T. Highly stereoselective synthesis of functionalized β,β-di- and trisubstituted vinylic sulfoxides by Cu-catalyzed conjugate addition of organozinc reagents. J. Org. Chem. 2004, 69, 8387–8393.
   Google Scholar
• (a) Simpkins , N. S. Sulfones in Organic Synthesis ; Pergamon Press : Oxford , UK , 1993; (b) Bäckvall, J. E.; Chinchilla, R.; Nájera, C.; Yus, M. The use of sulfonyl 1,3-dienes in organic synthesis. Chem. Rev. 1998, 98, 2291–2312.
   Google Scholar
• (a) Xie , M. H. ; Wang , J. L. ; Gu , X. X. ; Sun , Y. ; Wang , S. W. Highly regio- and stereoselective synthesis of tetrasubstituted olefins by the three-component tandem reaction of allylzinc bromide, acetylenic sulfone, and halohydrocarbon . Org. Lett. 2006 , 8 , 431 – 434 ; (b) Xie, M. H.; Huang, X. Carbomagnesiation of acetylenic sulfones catalyzed by CuCN and its application in the stereoselective synthesis of polysubstituted vinyl sulfones. Synlett 2003, 477–480.
   Google Scholar
• Smorada , R. L. ; Truce , W. E. Reactions of arylsulfonylacetylenes with organolithium and grignard reagents: A new synthesis of acetylenes . J. Org. Chem. 1979 , 44 , 3444 – 3445 .
   Web of Science ®Google Scholar
• (a) Hadani , A. N. ; Rawal , V. H. Stereospecific synthesis of highly substituted skipped dienes through multifunctional palladium catalysis . Org. Lett. 2002 , 4 , 4317 – 4320 ; (b) Okamoto, S.; Takayama, Y.; Gao, Y.; Sato, F. One-pot synthesis of a variety of 1,4-alkadienes and 1,2,4-alkatrienes from alkynes, allyl, or propargyl compounds and electrophiles by a (η2-propene)Ti(O-i-Pr)2-mediated reaction. Synthesis 2000, 975–979.
   Google Scholar
• Truce , W. E. ; Wolf , G. C. Adducts of sulfonyl iodides with acetylenes . J. Org. Chem. 1971 , 36 , 1727 – 1732 .
   Web of Science ®Google Scholar
• Love , B. E. ; Raje , P. S. ; Williams , T. C. Preparation of N-tosylaldimines . Synlett 1994 , 493 – 494 .
   Google Scholar