Improved synthesis of and nucleophilic addition to 2-formyl-2-cyclohexenone

TETRAHEDRON LETTERS

卷:56

Article

Adary, Elan M.¹  Chang, Chih-wei¹  D' Auria, Damian T.¹  Nguyen, Phuc M.¹  Polewacz, Klaudyna¹  Reinicke, Justin A.¹  Seo, Hannah¹  Berger, Gideon O.¹ 

[1] Hawaii Pacific Univ, Dept Nat Sci, Honolulu, HI 96813 USA

关键词: 2-Formyl-2-cyclohexenone;    2-Formyl-2-cycloalkenone;    Michael addition;    Dimethylmalonate;    Conjugate addition;   

DOI  :  10.1016/j.tetlet.2014.11.100

来源: Elsevier

【 摘 要 】

A preparation of 2-formyl-2-cyclohexenone in nearly quantitative yield and purity of approximately 95% is described. It is scalable and has been extended to the synthesis of the 5- and 7-membered ring homo-logs with comparable yields. Conditions have also been developed for the successful conjugate addition of dimethylmalonate to 2-formyl-2-cyclohexenone, in good and scalable yield (60%). This result has been extended to 5 other nucleophile classes, and the dimethylmalonate conjugate addition has been demonstrated with 2-formyl-2-cyclopentenone and 2-formyl-2-cycloheptenone. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

Free