Journal
ORGANIC LETTERS
Volume 21, Issue 17, Pages 7089-7093Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02658
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Funding
- National Natural Science Foundation of China [NNSFC 21871237, NNSFC 81330075]
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A highly efficient method for the enantioselective build of spiro[1-indanone-5,2'-gamma-butyrolactones] has been developed through the tandem Michael/transesterification reaction of alpha-hydroxy-l-indanone and alpha,beta-unsaturated esters. A broad range of spiro(1-indanone-butyrolacones) with contiguous stereocenters have been synthesized with excellent stereoselectivities (up to >20:1 dr, up to >99% ee) under the catalysis of dinuclear zinc complex. Moreover, the reaction can be run on a gram scale without affecting its stereoselectivities. A possible mechanism is proposed.
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