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Enantioselective Generation and Diastereoselective Reactions of Chiral Enolates Derived from α‐Heterosubstituted Carboxylic Acids . Preliminary Communication
Author(s) -
Seebach Dieter,
Naef Reto
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640829
Subject(s) - chemistry , enantioselective synthesis , mandelic acid , deprotonation , alkylation , halide , organic chemistry , alkyl , carboxylic acid , catalysis , ion
Abstract Dioxolanones 7 and 8a and oxazolinones 9a derived from pivalaldehyde and lactic acid, mandelic acid, and proline, respectively, furnish chiral enolates of type 3 by deprotonation with LDA. Reactions of these enolates with alkyl halides, aldehydes, and ketones (→ 8b, 9b, 11–13) are highly diastereoselective. Thus, the overall enantioselective α‐alkylation of chiral, non‐racemic α‐heterosubstituted carboxylic acids (4 → 6) is realized.