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Addition of the Lithium Anion of Diphenylmethanol Methyl/Methoxymethyl Ether to Nonracemic Sulfinimines: Two-Step Asymmetric Synthesis of Diphenylprolinol Methyl Ether and Chiral (Diphenylmethoxymethyl)amines

Author:
Reddy, Arava Amaranadha, Prasad, Kavirayani R.
Source:
Journal of organic chemistry 2018 v.83 no.18 pp. 10776-10785
ISSN:
1520-6904
Subject:
amines, catalytic activity, chemical reactions, enantiomers, ligands, lithium, methyl ethers, moieties
Abstract:
Addition of the lithium anion generated from diphenylmethanol methyl and methoxymethyl ether to nonracemic sulfinimines afforded the corresponding addition products in excellent diastereoselctivity and yields. Deprotection of the MOM as well as sulfinyl groups rendered the enantiopure (diphenylhydroxymethyl)amines in excellent yields. The procedure was applied for a two-step synthesis of diphenylprolinol, a privileged ligand in asymmetric catalysis.
Agid:
6146163