Asymmetric synthesis of (αS)-polyfluoroalkylated N-Boc-prolinols by the diethyl zinc-induced asymmetric Meerwein–Ponndorf–Verley reduction of perfluoroalkyl N-Boc-pyrrolidyl ketones

文献情報

出版日 2015-02-11

DOI 10.1039/C5QO00008D

インパクトファクター 5.281

著者

Kazumasa Funabiki, Hiroki Iwata, Yosuke Yano, Yasuhiro Kubota, Masaki Matsui

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要旨

The reduction of perfluoroalkyl N-Boc-pyrrolidyl ketones with diethyl zinc was investigated. As a result, asymmetric Meerwein–Ponndorf–Verley reduction of perfluoroalkyl N-Boc-pyrrolidyl ketones proceeded smoothly with the use of 5 equiv. of diethyl zinc as a reducing agent in hexane at room temperature to give (αS)-polyfluoroalkylated N-Boc-prolinols in good yields (31–73%) with high diastereomer ratios (up to αR/αS = 7/93). The absolute configuration at the α-position of the major diastereomer is opposite to that obtained by the reduction of N-Boc-pyrrolidyl ketone with NaBH4 in ethanol. Furthermore, we also achieved the tandem perfluorobutylation-MPV reduction of N-Boc-proline ethyl ester to give (αS)-perfluorobutylated N-Boc-prolinol as a sole diastereomer in 45% yield.

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Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Asymmetric synthesis of (αS)-polyfluoroalkylated N-Boc-prolinols by the diethyl zinc-induced asymmetric Meerwein–Ponndorf–Verley reduction of perfluoroalkyl N-Boc-pyrrolidyl ketones

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