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N1–C4 β‐Lactam Bond Cleavage in the 2‐(Trimethylsilyl)thiazole Addition to β‐Lactam Aldehydes: Asymmetric Synthesis of Spiranic and Tertiary α‐Alkoxy‐γ‐keto Acid Derivatives
Author(s) -
Alcaide Benito,
Almendros Pedro,
Redondo María C.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700231
Subject(s) - chemistry , lactam , enantiopure drug , thiazole , alkoxy group , trimethylsilyl , aldehyde , bond cleavage , cleavage (geology) , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , alkyl , geotechnical engineering , fracture (geology) , engineering
Abstract Starting substrates, enantiopure spiranic or 3‐substituted 3‐alkoxy‐4‐oxoazetidine‐2‐carbaldehydes, were prepared from ( R )‐2,3‐ O ‐isopropylideneglyceraldehyde derived azetidine‐2,3‐diones by sequential Barbier‐type addition reactions followed by hydroxy functionalization and aldehyde unmasking. The reaction between the above β‐lactam aldehydes and 2‐(trimethylsilyl)thiazole (TMST) gave as major products conformationally constrained α‐alkoxy‐γ‐keto amides, which can be considered both as aldols as well as Passerini‐type products, by N1–C4 β‐lactam bond cleavage. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)