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Racemization of α‐Alkyl‐β‐Keto Esters and Enantioselective Total Synthesis of Two C‐2′′′Epimers of Plant Glycerolipid Santinol C
Author(s) -
Wu WenJu,
Li MeiMei,
Liu Bo,
Wu Yikang
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900467
Subject(s) - racemization , enantiopure drug , chemistry , epimer , alkyl , enantioselective synthesis , stereochemistry , organic chemistry , catalysis
It is broadly believed that optically active α‐alkyl‐β‐keto esters racemize very quickly. Nevertheless, no one really knows how fast the racemization is. In fact, such species are hardly attainable to date. Now, a facile entry to these greatly understudied esters has been found and their racemization has been studied for the first time. The results showed that under neutral or slightly acidic conditions such species were much more stable than one might expect, though they did racemize rapidly under basic conditions. In light of the new findings, santinol C was also synthesized in enantiopure forms.