2016European Journal of Organic ChemistryRequires access

Organocatalytic Enantioselective Synthesis of P‐Stereogenic Chiral Oxazaphospholidines

Lanlan Wang, Zhijun Du, Qiang Wu, Rizhe Jin, Zheng Bian, Chuanqing Kang, Haiquan Guo, Xiaoye Ma, Lianxun Gao

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Abstract

Abstract The enantioselective synthesis of P‐stereogenic chiral organophosphines under organocatalysis is a challenging research field, and reports that use this approach are rare. Herein, we have developed the enantioselective synthesis of P‐stereogenic chiral oxazaphospholidines by using a bicyclic thiazole as the organocatalyst in the P–N and P–O bond‐forming reaction. The P‐chiral products were prepared in high yields with moderate enantioselectivities. The base that was used in this process had a significant influence on the enantioselectivity of the reaction and in some cases led to the opposite configuration of the P‐chiral center.

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What this paper is about

Abstract The enantioselective synthesis of P‐stereogenic chiral organophosphines under organocatalysis is a challenging research field, and reports that use this approach are rare. Herein, we have developed the enantioselective synthesis of P‐stereogenic chiral oxazaphospholidines by using a bicyclic thiazole as the organocatalyst in the P–N and P–O bond‐forming reaction. The P‐chiral products were prepared in high yields with moderate enantioselectivities. The base that was used in this process had a significant influence on the enantioselectivity of the reaction and in some cases led to the opposite configuration of the P‐chiral center.

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Available abstract

Abstract The enantioselective synthesis of P‐stereogenic chiral organophosphines under organocatalysis is a challenging research field, and reports that use this approach are rare. Herein, we have developed the enantioselective synthesis of P‐stereogenic chiral oxazaphospholidines by using a bicyclic thiazole as the organocatalyst in the P–N and P–O bond‐forming reaction. The P‐chiral products were prepared in high yields with moderate enantioselectivities. The base that was used in this process had a significant influence on the enantioselectivity of the reaction and in some cases led to the opposite configuration of the P‐chiral center.

Key concepts: Stereocenter, Enantioselective synthesis, Chemistry, Organocatalysis, Stereochemistry, Thiazole, Bicyclic molecule, Combinatorial chemistry

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