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Enantioselektive 1,4‐Additionen von metallorganischen Verbindungen an konjugierte Systeme im chiralen Medium DDB
Author(s) -
Langer Werner,
Seebach Dieter
Publication year - 1979
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.19790620604
Subject(s) - chemistry , enantioselective synthesis , enantiomer , conjugated system , ketene , medicinal chemistry , stereochemistry , organic chemistry , catalysis , polymer
Enantioselective 1,4‐additions of organometallic compounds to conjugated systems in the chiral medium DDB DDB = 1,4‐Dimethylamino‐2,3‐dimethoxybutan (= 2,3‐Dimethoxy‐ N , N , N ′, N ′‐tetramethyl‐1,4‐butandiamin). The chiral methoxyamine DDB is used as a cosolvent to add achiral Li‐, Cu‐, and Zn‐organic compounds enantioselectively to prochiral β‐carbon atoms of α, β‐unsaturated aldehydes, ketones, nitro compounds and ketene‐thioacetals ( Tables 1 and 2 ). The selectivity generally ranges from 55:45 to 63:27, in one case ( 9b ) an enantiomeric excess of 43% was obtained.