Simple amino silyl ether organocatalyst for asymmetric hetero Diels–Alder reaction of isatins with enones

Perumalsamy Parasuraman; Divakar Ganesan; Zubeda Begum; Chigusa Seki; Yuko Okuyama; Eunsang Kwon; Koji Uwai; Michio Tokiwa; Suguru Tokiwa; Mitsuhiro Takeshita; Hiroto Nakano

doi:10.1002/chir.23319

Simple amino silyl ether organocatalyst for asymmetric hetero Diels–Alder reaction of isatins with enones

Perumalsamy Parasuraman, Divakar Ganesan, Zubeda Begum, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano

SCI - Research and Analytical Center for Giant Molecules

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

Abstract

New two catalysts component system comprising of a primary β-amino silyl ethers as an organocatalyst and N-protected amino acids as a co-catalyst put together worked as an efficient organocatalyst system in the hetero Diels–Alder reaction of isatins with enones affording the chiral spirooxindole-tetrahydropyranones in good chemical yields and stereoselectivities (up to 94%, up to dr 78:22., up to 85% ee).

Original language	English
Pages (from-to)	454-464
Number of pages	11
Journal	Chirality
Volume	33
Issue number	8
DOIs	https://doi.org/10.1002/chir.23319
Publication status	Published - 2021 Aug

Keywords

hetero Diels–Alder reaction
organocatalysis
spirooxindole
β-amino alcohol
β-amino silyl ether

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/chir.23319

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title = "Simple amino silyl ether organocatalyst for asymmetric hetero Diels–Alder reaction of isatins with enones",

abstract = "New two catalysts component system comprising of a primary β-amino silyl ethers as an organocatalyst and N-protected amino acids as a co-catalyst put together worked as an efficient organocatalyst system in the hetero Diels–Alder reaction of isatins with enones affording the chiral spirooxindole-tetrahydropyranones in good chemical yields and stereoselectivities (up to 94%, up to dr 78:22., up to 85% ee).",

keywords = "hetero Diels–Alder reaction, organocatalysis, spirooxindole, β-amino alcohol, β-amino silyl ether",

author = "Perumalsamy Parasuraman and Divakar Ganesan and Zubeda Begum and Chigusa Seki and Yuko Okuyama and Eunsang Kwon and Koji Uwai and Michio Tokiwa and Suguru Tokiwa and Mitsuhiro Takeshita and Hiroto Nakano",

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year = "2021",

month = aug,

doi = "10.1002/chir.23319",

language = "English",

volume = "33",

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journal = "Chirality",

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T1 - Simple amino silyl ether organocatalyst for asymmetric hetero Diels–Alder reaction of isatins with enones

AU - Parasuraman, Perumalsamy

AU - Ganesan, Divakar

AU - Begum, Zubeda

AU - Seki, Chigusa

AU - Okuyama, Yuko

AU - Kwon, Eunsang

AU - Uwai, Koji

AU - Tokiwa, Michio

AU - Tokiwa, Suguru

AU - Takeshita, Mitsuhiro

AU - Nakano, Hiroto

PY - 2021/8

Y1 - 2021/8

N2 - New two catalysts component system comprising of a primary β-amino silyl ethers as an organocatalyst and N-protected amino acids as a co-catalyst put together worked as an efficient organocatalyst system in the hetero Diels–Alder reaction of isatins with enones affording the chiral spirooxindole-tetrahydropyranones in good chemical yields and stereoselectivities (up to 94%, up to dr 78:22., up to 85% ee).

AB - New two catalysts component system comprising of a primary β-amino silyl ethers as an organocatalyst and N-protected amino acids as a co-catalyst put together worked as an efficient organocatalyst system in the hetero Diels–Alder reaction of isatins with enones affording the chiral spirooxindole-tetrahydropyranones in good chemical yields and stereoselectivities (up to 94%, up to dr 78:22., up to 85% ee).

KW - hetero Diels–Alder reaction

KW - organocatalysis

KW - spirooxindole

KW - β-amino alcohol

KW - β-amino silyl ether

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U2 - 10.1002/chir.23319

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SN - 0899-0042

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ER -

Simple amino silyl ether organocatalyst for asymmetric hetero Diels–Alder reaction of isatins with enones

Abstract

Keywords

ASJC Scopus subject areas

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