Highly Diastereoselective Addition of Alkynylmagnesium Chlorides to N-tert-Butanesulfinyl Aldimines: A Practical and General Access to Chiral α-Branched Amines

被引：70

作者：

Chen, Bai-Ling ^{[1
]}

Wang, Bing ^{[1
,2
]}

Lin, Guo-Qiang ^{[1
,2
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

[2] Fudan Univ, Inst Biomed Sci, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 03期

基金：

中国国家自然科学基金;

关键词：

IRIDIUM-CATALYZED HYDROGENATION; ASYMMETRIC-SYNTHESIS; TETRAHYDROQUINOLINE ALKALOIDS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ARYLBORONIC ACIDS; TERMINAL ALKYNES; ALLYLIC AMINES; SOLVENT-FREE; IMINES;

D O I：

10.1021/jo902424m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of alkynylmagnesium chlorides to N-tert-butanesulfinyl imines proceeded with a remarkably high diastereoselectivity (dr > 13:1, mostly diastereopure), and with a general scope of both reaction partners. The high dr translated into simplified purification and higher optical purity for the synthesis of a wide array of chiral alpha-branched amines. The alkyne functionality also provides a multitude of opportunities for further synthetic transformations. The short asymmetric synthesis of (+)-angustureine 7 and (-)-cuspareine 10 was realized with use of this approach.

引用

页码：941 / 944

页数：4

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