Organocatalytic Stereoconvergent Synthesis of α-CF 3 Amides: Triketopiperazines and Their Heterocyclic Metamorphosis

Robert W. Foster; Eva N. Lenz; Nigel S. Simpkins; Darren Stead

doi:10.1002/chem.201701548

Organocatalytic Stereoconvergent Synthesis of α-CF 3 Amides: Triketopiperazines and Their Heterocyclic Metamorphosis

Robert W. Foster
, Eva N. Lenz
, Nigel S. Simpkins
, Darren Stead

Chemistry

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

The highly enantioselective alkylation of α-CF3 enolates, generated from triketopiperazines, has been accomplished through use of a bifunctional thiourea organocatalyst to facilitate 1,4-addition to varied enone acceptors. On treatment with appropriate nitrogen nucleophiles, the chiral triketopiperazine products undergo a metamorphosis, to provide novel fused heterocyclic lactams such as extended pyrazolopyrimidines.

Original language	English
Pages (from-to)	8810-8813
Journal	Chemistry: A European Journal
Volume	23
Issue number	37
Early online date	12 Jun 2017
DOIs	https://doi.org/10.1002/chem.201701548
Publication status	E-pub ahead of print - 12 Jun 2017

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http://doi.wiley.com/10.1002/chem.201701548

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abstract = "The highly enantioselective alkylation of α-CF3 enolates, generated from triketopiperazines, has been accomplished through use of a bifunctional thiourea organocatalyst to facilitate 1,4-addition to varied enone acceptors. On treatment with appropriate nitrogen nucleophiles, the chiral triketopiperazine products undergo a metamorphosis, to provide novel fused heterocyclic lactams such as extended pyrazolopyrimidines.",

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AU - Stead, Darren

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AB - The highly enantioselective alkylation of α-CF3 enolates, generated from triketopiperazines, has been accomplished through use of a bifunctional thiourea organocatalyst to facilitate 1,4-addition to varied enone acceptors. On treatment with appropriate nitrogen nucleophiles, the chiral triketopiperazine products undergo a metamorphosis, to provide novel fused heterocyclic lactams such as extended pyrazolopyrimidines.

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Organocatalytic Stereoconvergent Synthesis of α-CF 3 Amides: Triketopiperazines and Their Heterocyclic Metamorphosis

Abstract

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