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

共 45 条

[1] Morpholin-2-one Derivatives via Intramolecular Acid-Catalyzed Hydroamination [J].

Aldmairi, Abdul Hadi ;

Knight, David W. ;

Wirth, Thomas .

SYNTHESIS-STUTTGART, 2019, 51 (07) :1643-1648

[2] The market of chiral drugs: Chiral switches versus de novo enantiomerically pure compounds [J].

Calcaterra, Andrea ;

D'Acquarica, Ilaria .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2018, 147 :323-340

[3] A Concise Total Synthesis of (-)-HimalensineA [J].

Chen, Yuye ;

Hu, Jingping ;

Guo, Lian-Dong ;

Zhong, Weihe ;

Ning, Chengqing ;

Xu, Jing .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (22) :7390-7394

[4] Stereoselective Substitution of Configurationally Labile α-Bromo Arylacetates with Amines and Azlactones by L-Threonine-Mediated Crystallization-Induced Dynamic Resolution [J].

Choi, Yun Soo ;

Park, SeHee ;

Park, Yong Sun .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (14) :2539-2546

[5] Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps [J].

Coulthard, Graeme ;

Erb, William ;

Aggarwal, Varinder K. .

NATURE, 2012, 489 (7415) :278-281

[6] Mastering chiral substituted 2-oxopiperazines [J].

De Risi, Carmela ;

Pela, Michela ;

Pollini, Gian Piero ;

Trapella, Claudio ;

Zanirato, Vinicio .

TETRAHEDRON-ASYMMETRY, 2010, 21 (03) :255-274

[7] Syntheses and transformations of piperazinone rings. A review [J].

Dinsmore, CJ ;

Beshore, DC .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2002, 34 (04) :367-+

[8] Praziquantel and the control of schistosomiasis [J].

Doenhoff, MJ ;

Kimani, G ;

Cioli, D .

PARASITOLOGY TODAY, 2000, 16 (09) :364-366

[9] Synthesis of chiral piperazin-2-ones through palladium-catalyzed asymmetric hydrogenation of pyrazin-2-ols [J].

Feng, Guang-Shou ;

Zhao, Zi-Biao ;

Shi, Lei ;

Zhou, Yong-Gui .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (22) :6273-6278

[10] An efficient synthetic route to carbocyclic enaminonitriles via Lewis acid catalysed domino-ring-opening-cyclisation (DROC) of donor-acceptor cyclopropanes with malononitrile [J].

Ghorai, Manas K. ;

Talukdar, Ranadeep ;

Tiwari, Deo Prakash .

CHEMICAL COMMUNICATIONS, 2013, 49 (74) :8205-8207

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