# Desymmetrization of Bisallylic Amides: A Catalytic Enantioselective Diastereoselective Chlorocyclization Strategy

**Authors:** Yi Yi, Ankush Chakraborty, Xinliang Ding, Arvind Jaganathan, Neil Heberer, Babak Borhan

PMC · DOI: 10.1021/acs.orglett.5c01865 · 2025-07-01

## 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.

## Key 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).

## Linked entities

- **Chemicals:** N-chlorophthalimide (PubChem CID 18997), NCP (PubChem CID 16540), (DHQD)2PHAL (PubChem CID 11217202)

## Full-text entities

- **Chemicals:** N (MESH:D009584), -chlorophthalimide (-), oxazines (MESH:D010078)

## Figures

6 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12261326/full.md

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Source: https://tomesphere.com/paper/PMC12261326