Cinchonidinium acetate as a convenient catalyst for the asymmetric synthesis of cis-stilbenediamines

TETRAHEDRON LETTERS

卷:56

Article

Walvoord, Ryan R.¹  Kozlowski, Marisa C.¹ 

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

关键词: Aza-Henry;    Asymmetric organocatalysis;    Cinchona alkaloid;    Nitro-Mannich;    Vicinal diamine;   

DOI  :  10.1016/j.tetlet.2014.12.105

来源: Elsevier

【 摘 要 】

Inexpensive and readily available cinchonidinium acetate is an effective catalyst for the syrz-selective aza-Henry reaction of arylnitromethanes and aryl imines. The resulting masked cis-stilbenediamine products are produced in excellent diastereoselectivity and good enantioselectivity, and enantiopure material can be achieved via recrystallization. The features of the cinchona catalyst needed for selectivity are discussed, with specific emphasis on formation of a kinetically controlled syn-product without epimerization of the highly acidic alpha-nitro stereocenter. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

Free