Asymmetric Synthesis of 3, 4-Diaminochroman-2-ones Promoted by Guanidine and Bisguanidium Salt

作者：Dong Shunxi; Liu Xiaohua^*; Zhang Yulong; Lin Lili; Feng Xiaoming

来源：Organic Letters, 2011, 13(19): 5060-5063.

DOI：10.1021/ol2018888

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 center dot HBAr4F. In two cases, various substituted 3,4-dihydrocoumarins were obtained with high yields (up to 99%) as well as excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to >99:1 cis:trans and 98:2 trans:cis, respectively) under mild reaction conditions.

• 出版日期2011-10-7
• 单位四川大学