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Asymmetric Nucleophilic Acylation of Aldehydes via 1,1‐Heterodisubstituted Alkenes
Author(s) -
Monenschein Holger,
Dräger Gerald,
Jung Alexander,
Kirschning Andreas
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19990802)5:8<2270::aid-chem2270>3.0.co;2-l
Subject(s) - ketene , sharpless asymmetric dihydroxylation , chemistry , aldehyde , acylation , nucleophile , dihydroxylation , enantioselective synthesis , organic chemistry , stereochemistry , catalysis
Aldehydes can be efficiently acetylated in an asymmetric manner via 1,1‐heterodisubstituted alkenes. The method combines a homologation step of the starting aldehyde 1 followed by the Sharpless asymmetric dihydroxylation of intermediate prochiral 1,1‐heterodisubstituted alkenes 2 . The sequence works particularly well with ketene O , O ‐acetals as intermediates and allows the synthesis of α ‐hydroxy carboxylates 3 in high enantiopurity.