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. 2011 Jun 1;133(21):8134-7.
doi: 10.1021/ja202555m. Epub 2011 May 10.

Enantioselective dichlorination of allylic alcohols

K C Nicolaou  1 , Nicholas L Simmons, Yongcheng Ying, Philipp M Heretsch, Jason S Chen
Affiliations

Enantioselective dichlorination of allylic alcohols

K C Nicolaou et al. J Am Chem Soc. .

Abstract

The development of an enantioselective allylic alcohol dichlorination catalyzed by dimeric cinchona alkaloid derivatives and employing aryl iododichlorides as chlorine sources is reported. Reaction optimization, exploration of the substrate scope, and a model for stereoinduction are presented.

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Figures

Figure 1
Figure 1
Molecular structure of chlorosulfolipid cytotoxin 1, and opportunities for asymmetric allylic alcohol dichlorination.
Figure 2
Figure 2
Molecular structures and ORTEPs of p-nitrobenzoate esters 7′ and ent-10′.
Figure 3
Figure 3
Proposed stereoinduction model (11), and the molecular structure of (DHQ)2AQN.
Scheme 1
Scheme 1
Mechanism of Olefin Dichlorination and Challenges for Enantioselectivity
See this image and copyright information in PMC

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