Regio- and Stereoselective Synthesis of Functionalized Cyclopentene Derivatives via Mizoroki-Heck Reactions

被引：14

作者：

Wetzel, Alexander ^{[1
]}

Bergman, Joakim ^{[1
]}

Brandt, Peter ^{[2
]}

Larhed, Mats ^{[3
]}

Branalt, Jonas ^{[1
]}

机构：

[1] AstraZeneca, Dept Med Chem, Innovat Med & Early Dev Biotech Unit, Cardiovasc & Metab Dis, Pepparedsleden 1, SE-43183 Molndal, Sweden

[2] Uppsala Univ, BMC, Div Organ Pharmaceut Chem, Dept Med Chem, Box 574, SE-75123 Uppsala, Sweden

[3] Uppsala Univ, BMC, Sci Life Lab, Dept Med Chem, Box 574, SE-75123 Uppsala, Sweden

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 07期

关键词：

ARYLATION;

D O I：

10.1021/acs.orglett.7b00325

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd(0)-catalyzed Mizoroki-Heck alkenylations and arylations of protected aminocydopentenes, prepared, in a few steps from Vince lactam, afforded functionalized cyclopentenes in high yields and stereoselectivities. DFT calculations were performed to rationalize the high diastereoselectivities. Functionalized cyclopentene products were transformed into valuable chiral building blocks, such as cyclic gamma-amino acids and carbocyclic nucleoside precursors.

引用

页码：1602 / 1605

页数：4

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