Journal
ORGANIC LETTERS
Volume 19, Issue 7, Pages 1862-1865Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00625
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Funding
- National Natural Science Foundation of China [21542007]
- Program for New Century Excellent Talents in University [NCET-11-0053]
- Fundamental Research Funds of the Central Universities [DUT15TD25]
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A general and practical organocatalytic asymmetric 1,3-dipolar cycloaddition of 3-amino oxindole-based azomethine ylides and alpha,beta-enones has been developed. This reaction delivered spiro[pyrrolidine-2,3'-oxindole] products in high yields with excellent regio- and enantioselectivities (up to 99% yield, >20:1 rr, 99% ee). In addition, an array of spiro[dihydropyrrole-2,3'-oxindoles] were readily accessed by oxidative dehydrogenation. Notably, the inversion of the diastereoselectivity of the spiro[pyrrolidine-oxindole] product could be easily achieved through a facile oxidation-reduction process.
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