Journal
ORGANIC LETTERS
Volume 13, Issue 19, Pages 5060-5063Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol2018888
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Funding
- National Natural Science Foundation of China [20732003, 21021001, 21072133]
- Basic Research Program of China (973 Program) [2010CB833300]
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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.
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