Desymmetrization of Bisallylic Amides: A Catalytic Enantioselective Diastereoselective Chlorocyclization Strategy

TL;DR

A new catalytic method efficiently creates chiral compounds with three adjacent centers using chlorocyclization of bisallylic amides.

Contribution

A catalytic strategy for enantioselective and diastereoselective chlorocyclization of bisallylic amides is introduced.

Findings

Chlorinated oxazines with three contiguous chiral centers were synthesized in high yields.

The method achieved up to 99% enantioselectivity and high diastereoselectivity.

N-chlorophthalimide was used effectively as the chlorinating reagent.

Abstract

(DHQD)2PHAL-catalyzed diastereo­selective
and enantio­selective
chloro­cyclization reactions of bisallylic amides were achieved
with N-chloro­phthal­imide (NCP) as the
chlorinating reagent. A series of chlorinated oxazines bearing three
contiguous chiral centers were obtained in high yields (up to 99%),
high diastereo­selectivity
and excellent enantio­selectivity (up to 99% ee).

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