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Direct Diastereoselective Alkylation of Tartaric Acid Through an Enolate
Author(s) -
Naef Reto,
Seebach Dieter
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198110301
Subject(s) - electrophile , alkylation , tartaric acid , chemistry , tartrate , lithium (medication) , enantioselective synthesis , organic chemistry , stereochemistry , catalysis , biology , citric acid , endocrinology
The lithium enolates (1) of ( R,R )‐tartrate acetonides to not decompose with β‐elimination ; the are stable enough to be alkylated by reactive electrophiles to pentasubstituted trans ‐ and cis ‐dioxolanes (2) and (3) (80:20), respectively. This reaction provides a route to the synthesis of natural products such as piscidic acid.