Cinchona-based squaramide-catalysed cascade aza-Michael-Michael addition: Enantioselective construction of functionalized spirooxindole tetrahydroquinolines

Wen Yang; Da Ming Du

doi:10.1039/c3cc44930k

Cinchona-based squaramide-catalysed cascade aza-Michael-Michael addition: Enantioselective construction of functionalized spirooxindole tetrahydroquinolines

Wen Yang
, Da Ming Du^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

105 Citations (Scopus)

Abstract

An efficient enantioselective cascade aza-Michael-Michael addition reaction catalysed by a chiral bifunctional tertiary amine-squaramide catalyst has been developed. This cascade reaction proceeded well under mild conditions, furnishing highly functionalized spirooxindole tetrahydroquinolines with three contiguous stereocenters in excellent yields with excellent diastereoselectivities (>25:1 dr) and high enantioselectivities (up to 94% ee).

Original language	English
Pages (from-to)	8842-8844
Number of pages	3
Journal	Chemical Communications
Volume	49
Issue number	78
DOIs	https://doi.org/10.1039/c3cc44930k
Publication status	Published - 5 Sept 2013

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abstract = "An efficient enantioselective cascade aza-Michael-Michael addition reaction catalysed by a chiral bifunctional tertiary amine-squaramide catalyst has been developed. This cascade reaction proceeded well under mild conditions, furnishing highly functionalized spirooxindole tetrahydroquinolines with three contiguous stereocenters in excellent yields with excellent diastereoselectivities (>25:1 dr) and high enantioselectivities (up to 94\% ee).",

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AU - Du, Da Ming

PY - 2013/9/5

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N2 - An efficient enantioselective cascade aza-Michael-Michael addition reaction catalysed by a chiral bifunctional tertiary amine-squaramide catalyst has been developed. This cascade reaction proceeded well under mild conditions, furnishing highly functionalized spirooxindole tetrahydroquinolines with three contiguous stereocenters in excellent yields with excellent diastereoselectivities (>25:1 dr) and high enantioselectivities (up to 94% ee).

AB - An efficient enantioselective cascade aza-Michael-Michael addition reaction catalysed by a chiral bifunctional tertiary amine-squaramide catalyst has been developed. This cascade reaction proceeded well under mild conditions, furnishing highly functionalized spirooxindole tetrahydroquinolines with three contiguous stereocenters in excellent yields with excellent diastereoselectivities (>25:1 dr) and high enantioselectivities (up to 94% ee).

UR - https://www.scopus.com/pages/publications/84883729642

U2 - 10.1039/c3cc44930k

DO - 10.1039/c3cc44930k

M3 - Article

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AN - SCOPUS:84883729642

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Cinchona-based squaramide-catalysed cascade aza-Michael-Michael addition: Enantioselective construction of functionalized spirooxindole tetrahydroquinolines

Abstract

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