Asymmetric allylation. An effective strategy for the convergent synthesis of highly functionalized homoallylic alcohols

Tetrahedron Letters

Volumn 39, Issue 40, 1998, Pages 7251-7254

  Williams, David R ^a   Brooks, Dawn A ^a   Meyer, Kevin G ^a   Clark, Michael P ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE; ALKALOID; BORANE DERIVATIVE; HENNOXAZOLE A; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; SYNTHESIS;

EID: 0032192220     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01557-3     Document Type: Article

References (27)

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2. 1. For reviews see: Yamamoto, Y. Acc. Chem. Res. 1987, 20, 243. Roush, W.R. "Comprehensive Organic Synthesis," vol. 2, Trost, B.M.; Fleming, I., ed., Pergamon Press, Oxford, 1.
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18. 3SnCuLi, THF, -78 °C→ -40 °C
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20. 1H NMR analysis of the crude reaction mixture. Isolated product yields were determined following flash silica chromatography.
21. 13. Ohtami, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H.J. J. Org. Chem. 1991, 56, 1296.
22. 14. Maguire, R.J.; Mulzer, J.; Bats, J.W. Tetrahedron Lett. 1996, 37, 5487. Maguire, R.J.; Mulzer, J.; Bats, J.W. J. Org. Chem. 1996, 61, 6936. Boron trifluoride etherate-catalyzed reactions provided no diastereoselection for substrates in entry 3 (yield 93%).
23. 14. Maguire, R.J.; Mulzer, J.; Bats, J.W. Tetrahedron Lett. 1996, 37, 5487. Maguire, R.J.; Mulzer, J.; Bats, J.W. J. Org. Chem. 1996, 61, 6936. Boron trifluoride etherate-catalyzed reactions provided no diastereoselection for substrates in entry 3 (yield 93%).
24. 15. For other preparations of syn-1,4-diols: Nishigaichi, Y.; Takuma, A.; Jodai, A. Tetrahedron Lett. 1991, 32, 2383. Almendros, P.; Gruttadauria, M.; Helliwell, M.; Thomas, E.J. J. Chem. Soc., Perkin Trans I 1997, 2549. (see also Refs 7, and 13)
25. 15. For other preparations of syn-1,4-diols: Nishigaichi, Y.; Takuma, A.; Jodai, A. Tetrahedron Lett. 1991, 32, 2383. Almendros, P.; Gruttadauria, M.; Helliwell, M.; Thomas, E.J. J. Chem. Soc., Perkin Trans I 1997, 2549. (see also Refs 7, and 13)
26. 16. The observed diastereoselection in entry 4 reflects the purity of the starting epoxy-aldehyde (89% ee; ratio 17:1). When this is taken into account, the allylation proceeds in >40:1 diastereoselection. Boron trifluoride etherate-catalyzed reactions for substrates in entry 5 illustrate Felkin addition. (equation presented)
27. 17. When the enantiomeric purity of the starting stannane (90% ee) is taken into account, the allylation proceeds in >20:1 diastereoselection for the (R)-isomer.