An Enantioselective Decarboxylative Glycolate Aldol Reaction

被引：0
|
作者：
Rahman, Md. Ataur [1 ]
Rehan, Mohammad [1 ]
Cellnik, Torsten [1 ]
Ahuja, Brij Bhushan [1 ]
Healy, Alan R. [1 ]
机构：
[1] New York Univ Abu Dhabi NYUAD, Chem Program, Saadiyat Isl, U Arab Emirates
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 42期
关键词：
CATALYTIC ASYMMETRIC-SYNTHESIS; ACID-CONTROLLED SYNTHESIS; LEWIS-BASE ACTIVATION; HYDROXYKETONES; DERIVATIVES; THIOESTERS; KETONES;
D O I：
10.1021/acs.orglett.4c03251
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report the application of a benzyloxy-functionalized malonic acid half thioester as an activated ester equivalent in a highly enantioselective decarboxylative glycolate aldol reaction. This robust method operates at ambient temperature, tolerates air and moisture, and generates CO2 as the only byproduct. The synthetic applicability of the method is demonstrated by the large-scale enantiodivergent synthesis of alpha-benzyloxy-beta-hydroxybutyric acid thioester and its subsequent conversion to diverse polyoxygenated building blocks, deoxy-sugars, and (-)-angiopterlactone B.
引用
收藏
页码：9040 / 9045
页数：6
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