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  • Diastereo- and enantioselective [3 + 2] cycloaddition reaction of Morita-Baylis-Hillman carbonates of isatins with N-phenylmaleimide catalyzed by Me-DuPhos.

Diastereo- and enantioselective [3 + 2] cycloaddition reaction of Morita-Baylis-Hillman carbonates of isatins with N-phenylmaleimide catalyzed by Me-DuPhos.

The Journal of organic chemistry (2012-04-05)
Yan Wang, Li Liu, Tao Zhang, Neng-Jun Zhong, Dong Wang, Yong-Jun Chen
RÉSUMÉ

A Me-DuPhos-catalyzed efficient asymmetric [3 + 2] cycloaddition reaction between Morita-Baylis-Hillman carbonates of isatins and N-phenylmaleimide has been developed. This reaction constructs three chiral centers in one step to afford spirocyclopentaneoxindoles in good yields (up to 84%) with excellent diastereo- and enantioselectivies (up to 99% ee).

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Sigma-Aldrich
N-Phenylmaleimide, 97%