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

Reddy, Arava Amaranadha and Prasad, Kavirayani R (2018) 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. In: JOURNAL OF ORGANIC CHEMISTRY, 83 (18). pp. 10776-10785.

PDF Jou_Org_Che_83-18_10776_2018.pdf - Published Version Restricted to Registered users only Download (929kB) | Request a copy

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.

Item Type:	Journal Article
Publication:	JOURNAL OF ORGANIC CHEMISTRY
Publisher:	AMER CHEMICAL SOC
Additional Information:	Copy right for this article belong to AMER CHEMICAL SOC
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	17 Oct 2018 13:18
Last Modified:	17 Oct 2018 13:20
URI:	http://eprints.iisc.ac.in/id/eprint/60898

Actions (login required)

View Item