Asymmetric synthesis of α-amino-1,3-dithianes via Chiral N -phosphonyl imine-based umpolung reaction without using chromatography and recrystallization

Padmanabha V. Kattamuri, Teng Ai, Suresh Pindi, Yinwei Sun, Peng Gu, Min Shi, Guigen Li

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

A series of α-amino-1,3-dithianes have been synthesized via the asymmetric Umpolung reaction of 2-lithio-1,3-dithianes with chiral N-phosphonyl imines in good chemical yields (up to 82%) and good to excellent diastereoselectivities (>99:1). The manner by which chiral N-phosphonyl imines are slowly added into the solution of 2-lithio-1,3-dithiane was found to be crucial for achieving excellent diastereoselectivity. The current synthesis was proven to follow the GAP chemistry (group-assistant-purification chemistry) process, which avoids traditional purification techniques of chromatography or recrystallization, i.e., the pure chiral α-amino-1,3-dithianes attached with the chiral N-phosphonyl group were readily obtained by washing the solid crude products with hexane or a mixture of hexane-ethyl acetate.

Original languageEnglish
Pages (from-to)2792-2797
Number of pages6
JournalJournal of Organic Chemistry
Volume76
Issue number8
DOIs
StatePublished - Apr 15 2011

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