Enantioselective Direct anti-Selective Mannich-type Reactions Catalyzed by 3-Pyrrolidinecarboxylic Acid in the Presence of Potassium Carbonate: Addition of Potassium Carbonate Improves Enantioselectivities
Author(s) -
Yuvraj Garg,
Fujie Tanaka
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c01561
Subject(s) - chemistry , potassium carbonate , catalysis , cyclohexanone , potassium , enantioselective synthesis , organic chemistry , mannich reaction , selectivity , carbonate
Mannich-type reactions of cyclohexanone and related six-membered-ring ketones with N - p -methoxyphenyl-protected imines of arylaldehydes catalyzed by 3-pyrrolidinecarboxylic acid in the presence of K 2 CO 3 hat afford anti -isomers of the Mannich products with high diastereo- and enantioselectivities are reported. Addition of K 2 CO 3 improved the enantioselectivities of the reactions catalyzed by 3-pyrrolidinecarboxylic acid while retaining the anti -selectivity of the reaction. Thus, the use of K 2 CO 3 expands the scope of these organocatalytic reactions for providing the products with high enantioselectivities.
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