Solvolytic enolization of scytalone

被引：6

作者：

Basarab, GS

Jordan, DB

Zheng, YJ

机构：

[1] Dupont Co, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA

[2] DuPont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

[3] Dupont Co, Stine Haskell Res Ctr, Agr Prod, Newark, DE 19714 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 11期

关键词：

D O I：

10.1021/ol0058590

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The major conformation of scytalone has an envelope shape with C3 forming the flap and the C3 hydroxyl in the equatorial position as determined by quantum mechanical calculations and corroborated by NMR. The C2 axial pro-R is slower to exchange with solvent than the equatorial pro-S hydrogen. Modeling the transition state for enolate formation points to a deprotonation through the flipped envelope conformation in which the C3-hydroxyl and the C2 pro-S hydrogen are axial.

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页码：1541 / 1544

页数：4

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