ENANTIOCONTROLLED SYNTHESIS OF QUATERNARY CARBON CENTERS VIA ANIONIC OXY-COPE REARRANGEMENT - AN EFFICIENT SYNTHESIS OF (+)-DIHYDROMAYURONE

被引：45

作者：

LEE, E

SHIN, IJ

KIM, TS

机构：

[1] Department of Chemistry, College of Natural Sciences, Seoul National University

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 01期

关键词：

D O I：

10.1021/ja00157a041

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(+)-Dihydromayurone (1) was enantioselectively synthesized from β-cyclocitral (7). The key step in the synthesis involved anionic oxy-Cope rearrangement of allylic alcohol 6 to aldehyde 5. Efficient transfer of chirality from the secondary allylic alcohol center to the quaternary carbon center was observed via chairlike transition state with the equatorial oxyanionic bond. © 1990, American Chemical Society. All rights reserved.

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页码：260 / 264

页数：5

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