Organocatalytic and Regiodivergent Mannich Reaction of Ketones with Benzoxazinones

Organocatalytic and Regiodivergent Mannich Reaction of Ketones with Benzoxazinones

Abstract In this study, we have developed solvent‐controlled regioselective Mannich reaction of cyclicimines (benzoxazinones) with various ketones by using ʟ‐proline as catalyst to afford Mannich products in high yields with excellent enantio‐ and diastereoselectivity. The unsymmetrical ketones prod...

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Bibliographic Details
Published in:Advanced synthesis & catalysis Vol. 360; no. 23; pp. 4464 - 4469
Main Authors: Viji, Mayavan, Sim, Jaeuk, Li, Siyuan, Lee, Heesoon, Oh, Kyungsoo, Jung, Jae‐Kyung
Format: Journal Article
Language:English
Published: Heidelberg Wiley Subscription Services, Inc 03-12-2018
Subjects:
Chloroform
Ketones
Proline
Solvents
Stereoselectivity
Online Access:Get full text
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Summary:Abstract In this study, we have developed solvent‐controlled regioselective Mannich reaction of cyclicimines (benzoxazinones) with various ketones by using ʟ‐proline as catalyst to afford Mannich products in high yields with excellent enantio‐ and diastereoselectivity. The unsymmetrical ketones produced the linear isomer as the major product in chloroform solvent. On contrary, using the DMSO solvent favoured the formation of branch isomer product with excellent enantio‐ and diastereoselectivity. The aromatic auxiliary was successfully removed and afforded N ‐protected chiral amino acid derivative. magnified image
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800870