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A Diastereoselective Synthesis of β‐( N ‐Acylamino)aldehydes by Rearrangement of O ‐Vinyl‐ N,O ‐Acetals
Author(s) -
Frauenrath Herbert,
Arenz Thomas,
Raabe Gerhard,
Zorn Martin
Publication year - 1993
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199300831
Subject(s) - isomerization , chemistry , medicinal chemistry , organic chemistry , stereochemistry , catalysis
The isomerization of N ‐acyl O ‐allyl N,O acetals 1 to give compounds 2 and their subsequent reaction with Me 3 SiO 3 SCF 3 leads to novel acyclic β‐( N ‐acylamino)aldehydes 3 with high diastereoselectivity. These compounds could serve as valuable synthetic building blocks; their relative configurations were assigned by X‐ray structure analysis (for the compound in which R 1 Me, R 2 t Bu).