Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones

被引：7
|
作者：
Malapit, Christian A. [1 ,2 ]
Luvaga, Irungu K. [1 ]
Caldwell, Donald R. [1 ]
Schipper, Nicholas K. [1 ]
Howell, Amy R. [1 ]
机构：
[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA
[2] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 17期
基金：
美国国家卫生研究院;
关键词：
ASYMMETRIC-SYNTHESIS; ARYLBORONIC ACIDS; PROTEASOME INHIBITOR; CROSS-METATHESIS; NATURAL-PRODUCTS; 1,4-ADDITION; ORLISTAT; SYNTHASE; PROBES; LOCALIZATION;
D O I：
10.1021/acs.orglett.7b01994
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-step preparation of 3,4-disubstituted beta-lactones through Rh-catalyzed conjugate addition of aryl or alkenyl boronic acids to alpha-methylene-beta-lactones is described. The operationally simple, stereoselective transformation provides a broad range of beta-lactones from individual alpha-methylene-beta-lactone templates. This methodology allowed for a direct, final-step C-3 diversification of nocardiolactone, an antimicrobial natural product.
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页码：4460 / 4463
页数：4
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