Stereoselective Synthesis of Difunctionalized 1,3-Dienes Containing Silicon and Selenium via Hydrozirconation of (Z)-3-(Trimethylsilyl)alk-3-en-1-ynes

REFERENCES

• (a) Naso , F. Stereospecific synthesis of olefins through sequential cross- coupling reactions . Pure Appl. Chem. 1988 , 60 , 79 – 88 ; (b) Pearson , W. H. ; Lin , K.-C. ; Poon , Y.-F. A stereoselective route to 2-(phenylthio)-1,3-butadienes . J. Org. Chem. 1989 , 54 , 5814 – 5819 ; (c) Grieco , P. A. ; May , S. A. ; Kaufman , M. D. A new strategy for the preparation of 11-oxygenated steroids synthesis of (±)adrenosterone . Tetrahedron Lett. 1998 , 39 , 7047 – 7050 ; (d) Cai , M. ; Wang , D. ; Wang , P. Novel stereoselective synthesis of 1-substituted 1,3-dien-2-yl sulfides via Stille coupling reactions of (E)-α-stannylvinyl sulfides with alkenyl iodides . J. Organomet. Chem. 2006 , 691 , 737 – 741 .
   Web of Science ®Google Scholar
• (a) Camasseto , J. V. ; Brandt , C. A. Selenium in organic synthesis: A novel route to 1-phenylselenobutadienes and 1,4-dicarbonyl compounds . Synthesis 1987 , 146 – 148 ; (b) Hevesi , L. ; Hermans , B. ; Allard , C. Nickel and palladium catalyzed coupling of vinyl selenides with trimethylsilylmethylmagnesium chloride: A new synthesis of allyl silanes . Tetrahedron Lett. 1994 , 35 , 6729 – 6730 ; (c) Zhu , L. S. ; Huang , Z. Z. ; Huang , X. Stereoselective synthesis of (E,E)-1-arylselenobutadienes by cross-coupling reactions in the presence of palladium catalyst . Tetrahedron 1996 , 52 , 9819 – 9822 ; (d) Ma , Y. ; Huang , X. Novel stereoselective synthesis of 1,3-dienyl selenides by palladium–copper cocatalyzed cross coupling reaction of (E)-α-selanylvinylstannanes . J. Chem. Soc., Perkin Trans. 1997 , 1 , 2953 – 2955 .
   Google Scholar
• (a) Negishi , E. ; Luo , F. T. A stereoselective route to 2-(phenylthio)-1,3- butadienes . J. Org. Chem. 1983 , 48 , 1560 – 1562 ; (b) Luh , T.-Y. ; Wong , K.-T. Silyl-substituted conjugated dienes: Versatile building blocks in organic synthesis . Synthesis 1993 , 349 – 370 ; (c) Ni , Z.-J. ; Yang , P.-F. ; Ng , D. K. P. ; Tzeng , Y.-L. ; Luh , T.-Y. Transition metal promoted reaction, 34: Unified synthesis of vinylsilanes and silylated butadienes: Nickel-catalyzed olefination and silylolefination of dithioacetals . J. Am. Chem. Soc. 1990 , 112 , 9356 – 9364 .
   Web of Science ®Google Scholar
• (a) Suzenet , F. ; Blart , E. ; Quintard , J. P. Regio- and stereoselective synthesis of polyenic vinyltinacetals: The unexpected effect of the nature of a remote acetal function on the regioselectivity of the stannylmetalation . Synlett 1998 , 879 – 881 ; (b) Lipshutz , B. H. ; Lindsley , C. A streamlined route to highly conjugated, all-E polyenes characteristic of oxo polyene macrolide antibiotics . J. Am. Chem. Soc. 1997 , 119 , 4555 – 4556 ; (c) Betzer , J. F. ; Delaloge , F. ; Muller , B. ; Pancrazi , A. Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities . J. Org. Chem. 1997 , 62 , 7768 – 7780 .
   Google Scholar
• (a) Banert , K. ; Fendel , W. ; Schlott , J. Double functionalized dienes of 6 and 9 may find use as synthetic building blocks. Angew. Chem. Int. Ed. 1998, 37, 3289–3293; (b) Wang , C. ; Song , Q. ; Xi , Z. Reactions of 1,4-dilithiobutadienes with isothiocyanates: Preparation of iminocyclopentadiene derivatives via cleavage of the C=S double bond of a RN=C=S molecule. Tetrahedron 2004, 60, 5207–5214; (c) Banert , K. ; Schlott , J. Stereospecific synthesis of 1,2-difunctionalized buta-1,3-dienes via tandem [3,3]-[3,3] sigmatropic rearrangements. Tetrahedron 2000, 56, 5413–5419; (d) Li , J.-H. ; Liang , Y. ; Xie , Y.-X. Mild and selective palladium-catalyzed dimerization of terminal alkynes to form symmetrical (Z,Z)-1,4-dihalo-1,3-dienes. J. Org. Chem. 2004, 69, 8125–8127; (e) Shimizu , M. ; Kurahashi , T. ; Hiyama , T. Novel synthesis of 2,3-bisboryl-1,3-dienes from 1-bromo-1-lithioethene and 1,1-bisborylalkenes. Synlett 2001, 1006–1008; (f) Herndon , J. W. ; Patel , P. P. Reaction of propargylsilanes with chromium carbene complexes: Synthesis of conjugated diene enol ethers through a tandem alkyne insertion-1,2-silicon shift process. J. Org. Chem. 1996, 61, 4500–4501; (g) Desurmont , G. ; Dalton , S. ; Giolando , D. M. ; Srebnik , M. Sequential transformations of 1,3-dibora butadienes to enones or tetrasubstituted 1,3-butadienes. J. Org. Chem. 1996, 61, 7943–7946; (h) Lipshutz , B. H. ; Lee , J. I. A one-pot, lynchpin approach to 1,4-disubstituted E,E-butadienes via multiple cyanocuprate-mediated transmetalations. Tetrahedron Lett. 1991, 32, 7211–7214; (i) Babudri , F. ; Fiandanese , V. ; Mazzone , L. ; Naso , F. A general approach to conjugated (E,E)-dienes through sequential coupling reactions. Tetrahedron Lett. 1994, 35, 8847–8850.
   PubMedGoogle Scholar
• (a) Trost , B. M. ; Vladuchick , W. C. ; Bridges , A. J. Sulfur as a regiochemical control element: Cycloadditions of 2-alkoxy(acyloxy)-3-alkyl(aryl)thiobuta- 1,3-dienes . J. Am. Chem. Soc. 1980 , 102 , 3554 – 3572 ; (b) Padwa , A. ; Norman , B. H. Intramolecular cycloaddition reaction of oximes with vinyl sulfones . Tetrahedron Lett. 1988 , 29 , 2417 – 2419 ; (c) Pegram , J. J. ; Anderson , C. B. The synthesis of 1-benzyldimethylsilyl-4-phenylthio-1,3-butadiene: A new diene-regenerable Diels–Alder synthon . Tetrahedron Lett. 1988 , 29 , 6719 – 6720 ; (d) Padwa , A. ; Harrison , B. ; Norman , B. H. The uncatalyzed Diels–Alder reaction of imines with bis(phenylsulfonyl) substituted dienes . Tetrahedron Lett. 1989 , 30 , 3259 – 3262 ; (e) Aversa , M. C. ; Barattucci , A. ; Bonaccorsi , P. ; Giannetto , P. ; Jones , D. N. Synthesis and asymmetric Diels-Alder reactions of enantiopure 3-(alkylsulfinyl)-1-methoxy-1,3-butadienes . J. Org. Chem. 1997 , 62 , 4376 – 4384 .
   Google Scholar
• Su , M. ; Kang , Y. ; Yu , W. ; Hua , Z. ; Jin , Z. Negishi coupling between α-alkyl(aryl)thio vinyl zinc chloride and α-bromovinyl ether: A convergent synthesis of 2-alkoxy-3-alkyl(aryl)thiobuta-1,3-dienes . Org. Lett. 2002 , 4 , 691 – 694 .
   PubMedGoogle Scholar
• Coleman , R. S. ; Walczak , M. C. Tandem Still/Suzuki coupling of a hetero-bis-metalated diene . Org. Lett. 2005 , 7 , 2289 – 2291 .
   PubMedGoogle Scholar
• Cai , M.-Z. ; Zhou , Z. ; Wang , P.-P. A facile stereoselective synthesis of difunctionalized 1,3-dienes containing silicon and tin via palladium-catalyzed cross-coupling reaction. Synthesis 2006, 789–793.
   Google Scholar
• Tsushima , K. ; Murai , A. Total synthesis of (+)-laurencin . Tetrahedron Lett. 1992 , 33 , 4345 – 4348 , and references therein.
   Google Scholar
• Gao , L.-X. ; Murai , A. Total synthesis of (−)-dactylyne and (−)-isodactylyne . Tetrahedron Lett. 1992 , 33 , 4349 – 4352 , and references therein.
   Google Scholar
• Maloney , K. M. ; Danheiser , R. L. Total synthesis of quinolizidine alkaloid (−)-217A. Application of iminoacetonitrile cycloadditions in organic synthesis . Org. Lett. 2005 , 7 , 3115 – 3118 , and references therein .
   PubMedGoogle Scholar
• (a) Karle , I. L. Structure of dihydroisohistrionicotoxin, a unique unsaturated alkaloid and anticholinergic agent . J. Am. Chem. Soc. 1973 , 95 , 4036 – 4040 ; (b) Stork , G. ; Zhao , K. Total syntheses of (−)-histrionicotoxin and (−)-histrioni- cotoxin 235A . J. Am. Chem. Soc. 1990 , 112 , 5875 – 5876 .
   PubMedGoogle Scholar
• Hoshi , M. ; Kawamura , N. ; Shirakawa , K. Construction of terminal conjugated enynes: Cu-mediated cross-coupling reaction of alkenyldialkylborane with (trimethylsilyl)ethynyl bromide . Synthesis 2006 , 1961 – 1970 .
   Google Scholar
• (a) Sonogashira , K. ; Tohda , Y. ; Hagihara , N. A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes, and bromopyridines . Tetrahedron Lett. 1975 , 4467 – 4470 ; (b) Sonogashira, K. Comprehensive Organic Synthesis; B. M. Trost, I. Fleming (Eds.); Pergamon Press: Oxford, 1991; vol. 3, chap. 2.4, pp. 521–549, and references therein .
   Google Scholar
• Kusumoto , T. ; Ando , K. ; Hiyama , T. Hydrosilylation of 1,4-bis-(trimethylsilyl)butadiynes and silyl-substituted butenynes . Bull. Chem. Soc. Jpn. 1992 , 65 , 1280 – 1290 .
   Google Scholar
• (a) Schwartz , J. ; Labinger , J. A. Hydrozirconation: A new transition metal reagent for organic synthesis . Angew. Chem. Int. Ed. 1976 , 15 , 333 – 340 ; (b) Hart , D. W. ; Blackburn , T. F. ; Schwartz , J. Hydrozirconation, III: Stereospecific and regioselective functionalization of alkylacetylenes via vinylzirconium(IV) intermediates . J. Am. Chem. Soc. 1975 , 97 , 679 – 680 .
   Web of Science ®Google Scholar
• (a) Deloux , L. ; Srebnik , M. Preparation of (Z)-1-alkenyl dioxaborolanes by hydrolysis of boryl zirconocene 1,1-dimetalloalkenes . J. Org. Chem. 1994 , 59 , 6871 – 6873 ; (b) Dabdoub , M. J. ; Baroni , A. C. M. Hydrozirconation of stannyl-acetylenes: Synthesis and reactions of ketene stannyl(telluro) acetals . J. Org. Chem. 2000 , 65 , 54 – 60 ; (c) Arefolov , A. ; Langille , N. F. ; Panek , J. S. Stereoselective synthesis of functionalized trisubstituted olefins via palladium(0)-catalyzed cross-coupling reaction . Org. Lett. 2001 , 3 , 3281 – 3284 ; (d) Huang , X. ; Duan , D. ; Zheng , W. Studies on hydrozirconation of 1-alkynyl sulfoxides or sulfones and the application for the synthesis of stereodefined vinyl sulfoxides or sulfones . J. Org. Chem. 2003 , 68 , 1958 – 1963 .
   Google Scholar
• Fryzuk , M. D. ; Bates , G. S. ; Stone , C. Preparation and isomerization of 1-phenylseleno 1,3-dienes . J. Org. Chem. 1991 , 56 , 7201 – 7211 .
   Google Scholar
• Cai , M. ; Huang , J. ; Ye , X. ; Song , C. Stereoselective synthesis of (E)-α-halovinylsilanes via hydrozirconation of alkynylsilanes . J. Chem. Res. 2003 , 770 – 772 .
   Google Scholar