Cyclic Model for the Asymmetric Conjugate Addition of Organolithiums with Enoates

被引：4

作者：

Nishimura, Katsumi ^{[1
]}

Fukuyama, Naoshi ^{[1
]}

Yamashita, Mitsuaki ^{[1
]}

Sumiyoshi, Takaaki ^{[1
]}

Yamamoto, Yasutomo ^{[2
]}

Yamada, Ken-ichi ^{[1
]}

Tomioka, Kiyoshi ^{[1
,2
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Doshisha Womens Coll Liberal Arts, Fac Pharmaceut Sci, Kodo, Kyotanabe 6100395, Japan

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 15期

关键词：

chiral ligand; asymmetric synthesis; organolithiums; conjugate addition; cascade reaction; CHIRAL DIETHER; ALPHA; BETA-UNSATURATED ESTERS; MICHAEL CYCLIZATION; REAGENTS; LIGAND; ACID; 1,4-ADDITION; DERIVATIVES; ANNULATION; AGONIST;

D O I：

10.1055/s-0034-1380702

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral diether ligand controlled asymmetric conjugate addition of organolithiums to nona-2,7-dienedioates preferentially proceeds via the s-cis conformation with coordination of the carbonyl oxygen atom to the lithium to give a lithium E-enolate intermediate. Subsequent intramolecular conjugate addition of the enolate also proceeds via a cyclic transition state involving the lithium and the s-cis-enoate, resulting in trans,trans-trisubstituted cyclohexanes with high enantiomeric excesses and yields.

引用

页码：2256 / 2264

页数：9

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