Diastereoselective addition of alkynylstannanes to alpha stannyl substituted mixed acetals: Synthesis of precursors for allenyl carbinols

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3819-3822

  Linderman, Russell J ^a   Chen, Sanyou ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ETHER DERIVATIVE; STANNANE DERIVATIVE; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; GAS CHROMATOGRAPHY; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 0029894944     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00722-8     Document Type: Article

References (18)

1. Marshall, J.A.; Schon, C.A. J. Org. Chem. 1995, 60, 5966-5968, and earlier references therein.
2. Marshall, J.A.; Wang, X.-J. J. Org. Chem. 1991, 56, 960-969.
3. (a) Marshall, J.A.; Perkins, J. J. Org. Chem. 1994, 59, 3509-3511.
4. (b) Marshall, J.A.; Wang, X.-J. J. Org. Chem. 1991, 56, 4913-4918.
5. For a review of the [2,3]-Wittig rearrangement, see: Nakai, T.; Mikami, K. Org. Reactions 1994, 46, 105-209. In one case, Nakai and co-workers have carried out the [2,3]-Wittig rearrangment on a more substituted stannane obtained by an O-alkylation route, see: Tomooka, K.; Igarashi, T.; Nakai, T. Tetrahedron 1994, 50, 13417-13424.
6. For a review of the [2,3]-Wittig rearrangement, see: Nakai, T.; Mikami, K. Org. Reactions 1994, 46, 105-209. In one case, Nakai and co-workers have carried out the [2,3]-Wittig rearrangment on a more substituted stannane obtained by an O-alkylation route, see: Tomooka, K.; Igarashi, T.; Nakai, T. Tetrahedron 1994, 50, 13417-13424.
7. Linderman, R.J.; Chen, S. Tetrahedron Lett. 1995, 36, 7799-7802.
8. (a) Himbert, G.; Henn, L. Tetrahedron Lett. 1981, 22, 2637-2640.
9. (b) Himbert, G. Angew. Chem. Int. Ed. Engl. 1979, 405-406.
10. (c) Himbert, G.; Schwickerath, W. Ann. Chem. 1983, 1185-1193.
11. Konig, K.; Neumann, W.P. Tetrahedron Lett. 1967, 495-498.
12. For examples of palladium catalyzed coupling reactions of alkynylstannanes with a number of electrophiles, see: Hegedus, L.S. Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, CA. 1994.
13. Logue, M.W.; Teng, K. J. Org. Chem. 1982, 47, 2549-2553.
14. Jousseaume, B.; Villeneuve, P. Tetrahedron 1989, 45, 1145-1154.
15. Linderman, R.J.; Anklekar, T.V. J. Org. Chem. 1992, 50, 5078-5080. In addition, further unpublished work in this laboratory (S. Chen) on vinyl copper addition reactions (see reference 5) has fully defined the relative and absolute stereochemistry of the addition products by chemical correlation.
16. 1H-NMR integration.
17. 1H-NMR by the methoxy signal at 3.48 ppm and the methine quartet at 4.29 ppm.
18. 2) using hexane as the eluent. All new compounds exhibited correct spectral and analytical (CH combustion, MS) data.