Organic letters

Asymmetric synthesis of 3, 4-Diaminochroman-2-ones promoted by guanidine and bisguanidium salt

S Dong, X Liu, Y Zhang, L Lin, X Feng

Index: Dong, Shunxi; Liu, Xiaohua; Zhang, Yulong; Lin, Lili; Feng, Xiaoming Organic Letters, 2011 ,  vol. 13,  # 19  p. 5060 - 5063

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Citation Number: 42

Abstract

A highly enantioselective synthesis of 3, 4-diaminochroman-2-ones has been realized via the domino reaction of o-hydroxy aromatic aldimines and azlactones. Notably, a cis-product was obtained as the major product by the use of guanidine 2a whereas a trans-product was the major product with bisguanidium salt 3• HBArF4. In two cases, various substituted 3, 4- dihydrocoumarins were obtained with high yields (up to 99%) as well as excellent ...