Rational design of highly effective asymmetric Diels-Alder catalysts bearing 4,4́-sulfonamidomethyl groups

Akira Sakakura; Rei Kondo; Yuki Matsumura; Matsujiro Akakura; Kazuaki Ishihara

doi:10.1021/ja906098b

Rational design of highly effective asymmetric Diels-Alder catalysts bearing 4,4́-sulfonamidomethyl groups

Akira Sakakura, Rei Kondo, Yuki Matsumura, Matsujiro Akakura, Kazuaki Ishihara

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

51 Citations (Scopus)

Abstract

(Chemical Equation Presented) The rational design of bis(oxazoline)- copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,4́-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.

Original language	English
Pages (from-to)	17762-17764
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	131
Issue number	49
DOIs	https://doi.org/10.1021/ja906098b
Publication status	Published - Dec 16 2009
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Rational design of highly effective asymmetric Diels-Alder catalysts bearing 4,{\'4}-sulfonamidomethyl groups",

abstract = "(Chemical Equation Presented) The rational design of bis(oxazoline)- copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,{\'4}-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.",

author = "Akira Sakakura and Rei Kondo and Yuki Matsumura and Matsujiro Akakura and Kazuaki Ishihara",

year = "2009",

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AU - Sakakura, Akira

AU - Kondo, Rei

AU - Matsumura, Yuki

AU - Akakura, Matsujiro

AU - Ishihara, Kazuaki

PY - 2009/12/16

Y1 - 2009/12/16

N2 - (Chemical Equation Presented) The rational design of bis(oxazoline)- copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,4́-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.

AB - (Chemical Equation Presented) The rational design of bis(oxazoline)- copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,4́-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.

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Rational design of highly effective asymmetric Diels-Alder catalysts bearing 4,4́-sulfonamidomethyl groups

Abstract

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