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Organocatalytic and Regiodivergent Mannich Reaction of Ketones with Benzoxazinones
Author(s) -
Viji Mayavan,
Sim Jaeuk,
Li Siyuan,
Lee Heesoon,
Oh Kyungsoo,
Jung JaeKyung
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800870
Subject(s) - chemistry , regioselectivity , mannich reaction , solvent , chloroform , organic chemistry , catalysis , derivative (finance) , organocatalysis , combinatorial chemistry , enantioselective synthesis , financial economics , economics
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.