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L‐Proline‐Catalyzed One‐Pot Diastereoselective Synthesis of Cyclohexanols from β‐Aryl‐γ‐nitroketones and α,β‐Unsaturated Aldehydes: A New Route to 2,3,4,6‐Tetrasubstituted Phenols
Author(s) -
Yadav Anubha,
Srivastava Anvita,
Mobin Shaikh M.,
Samanta Sampak
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803521
Subject(s) - cyclohexanol , chemistry , aryl , catalysis , aldol reaction , phenols , domino , functional group , combinatorial chemistry , reaction conditions , organic chemistry , cyclohexanone , proline , alkyl , polymer , biochemistry , amino acid
A wide array of densely functionalized cyclohexanol derivatives having five contiguous chiral centers were efficiently achieved in good to high yields with high diastereoselectivities. The double C−C bonds forming reaction proceeds via a domino nitro‐Michael/aldol reaction between several β‐aryl‐substituted‐γ‐nitroketones and a range of β‐aryl‐substituted acroleins as Michael acceptors catalyzed by L‐proline as a naturally available, non‐toxic, cheap organocatalyst. Several important features of this strategy include 100% atom‐economical, high‐efficiency, operational simplicity, and broad functional‐group tolerance. Gratifyingly, one‐pot conversion of cyclohexanols to a novel class of 2,3,4,6‐tetrasubstituted phenols under metal‐free conditions has been demonstrated.