Highly Stereoselective Synthesis of Terminal Chloro-Substituted Propargylamines and Further Functionalization

被引：9

作者：

Jordan, Savannah ^{[1
]}

Starks, Samuel A. ^{[1
]}

Whatley, Michael F. ^{[1
]}

Turlington, Mark ^{[1
]}

机构：

[1] Berry Coll, Dept Chem, Mt Berry, GA 30149 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 19期

关键词：

ENANTIOSELECTIVE 3-COMPONENT SYNTHESIS; PROMOTED DIASTEREOSELECTIVE SYNTHESIS; ZINC/BINOL-CATALYZED ALKYNYLATION; OPTICALLY-ACTIVE PROPARGYLAMINES; CHIRAL PROPARGYLAMINES; ASYMMETRIC-SYNTHESIS; AMINES; CYCLOISOMERIZATION; ALDIMINES; ALDEHYDES;

D O I：

10.1021/acs.orglett.5b02408

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly stereoselective addition of lithiated chloroacetylene, derived in situ from cis-1,2-dichloroethene and methyl lithium, to Ellman chiral N-tert-butanesulfinyl imines is reported. The reaction proceeds in high yield (up to 98%) and with excellent diastereoselectivity (up to >20:1) for a variety of aryl, heteroaromatic, alkyl, and alpha,beta-unsaturated imine substrates. Transformations of the terminal chloro-substituted propargylamine products are described in which lithium-halogen exchange yields nucleophilic acetylides that can be quenched to yield terminal alkynes or intercepted by carbon electrophiles.

引用

页码：4842 / 4845

页数：4

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