Asymmetric Catalytic Access to Piperazin-2-ones and Morpholin-2-ones in a One-Pot Approach: Rapid Synthesis of an Intermediate to Aprepitant

被引：9

作者：

Meninno, Sara ^{[1
]}

Lattanzi, Alessandra ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim & Biol A Zambelli, I-84084 Fisciano, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 12期

关键词：

RING-OPENING-CYCLIZATION; ENANTIOSELECTIVE SYNTHESIS; ORGANOCATALYTIC SYNTHESIS; ACTIVATED AZIRIDINES; RECEPTOR ANTAGONIST; PIPERAZINONE RINGS; EPOXIDATION; PSEUDOTHEONAMIDES; 2-OXOPIPERAZINES; DERIVATIVES;

D O I：

10.1021/acs.joc.2c02491

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot Knoevenagel reaction/asymmetric epoxidation/domino ring-opening cyclization (DROC) has been developed from commercial aldehydes, (phenylsulfonyl)acetonitrile, cumyl hydroperoxide, 1,2-ethylendiamines, and 1,2 ethanol amines to provide 3-aryl/alkyl piperazin-2-ones and morpholin-2-ones in yields of 38 to 90% and up to 99% ee. Two out of the three steps are stereoselectively catalyzed by a quinine derived urea. The sequence has been applied for a short enantioselective entry to a key intermediate, in both absolute configurations, involved in the synthesis of the potent antiemetic drug Aprepitant.

引用

页码：7888 / 7892

页数：5

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