A Diastereoselective Synthesis of β‐( N ‐Acylamino)aldehydes by Rearrangement of  O ‐Vinyl‐ N,O ‐Acetals | Zendy

Frauenrath Herbert | Zendy; Arenz Thomas | Zendy; Raabe Gerhard | Zendy; Zorn Martin | Zendy

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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).

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