Enantioselective Generation and Diastereoselective Reactions of Chiral Enolates Derived from α‐Heterosubstituted Carboxylic Acids . Preliminary Communication | Zendy

Seebach Dieter | Zendy; Naef Reto | Zendy

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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

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.

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