(手性)双膦配体 Me-DuPhos 催化的异吲哚啉-3-酮的 Morita-Baylis-Hillman 碳酸酯与 N- 苯基马来酰亚胺的非对映和对映选择性 [3 + 2] 环加成反应。
Diastereo- and enantioselective [3 + 2] cycloaddition reaction of Morita-Baylis-Hillman carbonates of isatins with N-phenylmaleimide catalyzed by Me-DuPhos.
机构信息
Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
出版信息
J Org Chem. 2012 Apr 20;77(8):4143-7. doi: 10.1021/jo3002535. Epub 2012 Apr 10.
PMID:22471756
Abstract
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).
摘要
一种由 Me-DuPhos 催化的高效不对称 [3 + 2] 环加成反应已经被开发出来，该反应涉及到色酮的 Morita-Baylis-Hillman 碳酸酯和 N-苯基马来酰亚胺之间的反应。该反应在一步反应中构建了三个手性中心，以高产率（高达 84%）和优异的非对映选择性和对映选择性（高达 99%ee）得到螺环戊烷氧吲哚。
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