Allylic Substitution of Esters Derived from 2-Bromocyclohex-2-enol with Aryl Copper Reagents and Synthetic Utilization of the Derived anti SN2' Products

被引：5

作者：

Ikoma, Atsushi ^{[1
]}

Kobayashi, Yuichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Bioengn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

SYNLETT | 2014年 / 25卷 / 08期

关键词：

allylic substitution; bromocyclohex-2-enol; copper; Grignard reagent; patchouli alcohol; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CROSS-COUPLING REACTIONS; PATCHOULI ALCOHOL; KINETIC RESOLUTION; GRIGNARD-REAGENTS; DERIVATIVES; CYCLIZATION; RAW264.7; INDOLES; ROUTE;

D O I：

10.1055/s-0033-1341065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylic substitution of esters derived from 2-bromocyclohex-2-enol with PhMgBr-based copper reagent was investigated to find high anti S(N)2' selectivity with the diethyl phosphate, whereas other esters such as picolinate, acetate, and mesylate resulted in partial racemization or recovery of the starting esters. This protocol was applied to the copper reagent derived from 2-Me-4-MeOC6H3MgBr and CuBrSMe2 and the olefin part of the anti S(N)2' product was cleaved for a synthesis of patchouli alcohol.

引用

页码：1150 / 1154

页数：5

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