Synthesis of Boc-protected 4, 5-methano-β-proline

AV Tymtsunik, YM Ivon, IV Komarov, OO Grygorenko

Index: Tymtsunik, Andriy V.; Ivon, Yevhen M.; Komarov, Igor V.; Grygorenko, Oleksandr O. Tetrahedron Letters, 2014 , vol. 55, # 22 p. 3312 - 3315

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Citation Number: 4

Abstract

Abstract An efficient method for the preparation of Boc-protected 4, 5-methano-β-proline—a novel bicyclic cyclopropane-containing β-amino acid—was developed, starting from readily available itaconic acid. A modified Simmons–Smith reaction was used for the construction of the cyclopropane ring. The method allowed for the synthesis of both cis and trans isomers of the title compound in 49% total yield and can be employed for gram-scale preparations. ...