Stereoselective Synthesis of Secondary and Tertiary Boronic Esters via Matteson Homologation

被引：2
|
作者：
Tost, Markus [1 ]
Kazmaier, Uli [1 ]
机构：
[1] Saarland Univ, Organ Chem 1, D-66123 Saarbrucken, Germany
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 37期
关键词：
PROTECTED SIDE-CHAIN; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; REAGENTS;
D O I：
10.1021/acs.orglett.3c02360
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Matteson homologations of chiral boronic esters with lithium dichlorocarbenoids and various nucleophiles proved to be a useful method for the synthesis of functionalized polyketides in a highly stereoselective fashion. Via repeated homologation steps, only 1,2-anti- and 1,3-syn-configured products were obtained. Homologation with substituted carbenoids followed by reaction with carbon nucleophiles resulted in configurationally inverted products and tertiary boronic esters in a highly stereoselective fashion. This approach significantly expands the potential of the Matteson reaction.
引用
收藏
页码：6835 / 6839
页数：5
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