ADDITION OF ORGANOCOPPER REAGENTS TO CYCLIC SULFITES OR CARBONATES OF GAMMA,DELTA-DIHYDROXY (E)-ALPHA,BETA-ENOATES

被引：15

作者：

KANG, SK

PARK, YW

LEE, DH

SIM, HS

JEON, JH

机构：

[1] Department of Chemistry, Sung Kyun Kwan University, Suwon, 440-746, Natural Science Campus

来源：

TETRAHEDRON-ASYMMETRY | 1992年 / 3卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(00)80506-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reaction of cyclic sulfites or carbonates of gamma,delta-dihydroxy (E)-alpha,beta-enoates with R2Cu(CN)Li2, BF3; RCu(CN)Li, BF3 (R = Me-,n-Bu-)afforded either diastereoselective S(N)2' products or reductive elimination product depending on reaction conditions. Addition of R2Cu(CN)Li2, BF3 (R = Me-, n-Bu-) to cyclic sulfite (1) or cyclic carbonate (3) (inverse addition) afforded highly regio-, (E)-stereo- and diastereoselectively alpha-alkylation products (6 and 8). By using this methodology, (2S, 5S)-trans-2-methyl-5-hexanolide, the pheromone of the carpenter bee Xylocopa hirutissima was synthesized.

引用

页码：705 / 708

页数：4

共 18 条

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[2]

BERNARDI R, 1989, SYNTHESIS-STUTTGART, P938

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