Asymmetric catalysis of (Hetero) diels-alder cycloadditions by a modified binaphthol-derived titanium complex

Yukihiro Motoyama; Masahiro Terada; Koichi Mikami

doi:10.1055/s-1995-5138

Asymmetric catalysis of (Hetero) diels-alder cycloadditions by a modified binaphthol-derived titanium complex

Yukihiro Motoyama, Masahiro Terada, Koichi Mikami

SCI - Chemistry

Tokyo Institute of Technology

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

34 Citations (Scopus)

Abstract

A chiral titanium complex 1a derived from 6,6'-dibromo-1,1'-bi-2-naphthol is found to give higher endo- and enantioselectivity along with higher catalytic activity than the parent binaphthol-derived titanium complex 1b in the (hetero) Diels-Alder reactions of 1-methoxydienes (2a and 2c) with methacrolein and glyoxylate but not with bromoacrolein.

Original language	English
Pages (from-to)	967-968
Number of pages	2
Journal	Synlett
Volume	1995
Issue number	9
DOIs	https://doi.org/10.1055/s-1995-5138
Publication status	Published - 1995 Sept

Keywords

(hetero) Diels-Alder reaction
asymmetric catalysis
binaphthol
enantioselectivity
Lewis acid
titanium complex

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10.1055/s-1995-5138

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title = "Asymmetric catalysis of (Hetero) diels-alder cycloadditions by a modified binaphthol-derived titanium complex",

abstract = "A chiral titanium complex 1a derived from 6,6'-dibromo-1,1'-bi-2-naphthol is found to give higher endo- and enantioselectivity along with higher catalytic activity than the parent binaphthol-derived titanium complex 1b in the (hetero) Diels-Alder reactions of 1-methoxydienes (2a and 2c) with methacrolein and glyoxylate but not with bromoacrolein.",

keywords = "(hetero) Diels-Alder reaction, asymmetric catalysis, binaphthol, enantioselectivity, Lewis acid, titanium complex",

author = "Yukihiro Motoyama and Masahiro Terada and Koichi Mikami",

note = "Publisher Copyright: {\textcopyright} 1995 Georg Thieme Verlag.",

year = "1995",

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doi = "10.1055/s-1995-5138",

language = "English",

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T1 - Asymmetric catalysis of (Hetero) diels-alder cycloadditions by a modified binaphthol-derived titanium complex

AU - Motoyama, Yukihiro

AU - Terada, Masahiro

AU - Mikami, Koichi

PY - 1995/9

Y1 - 1995/9

N2 - A chiral titanium complex 1a derived from 6,6'-dibromo-1,1'-bi-2-naphthol is found to give higher endo- and enantioselectivity along with higher catalytic activity than the parent binaphthol-derived titanium complex 1b in the (hetero) Diels-Alder reactions of 1-methoxydienes (2a and 2c) with methacrolein and glyoxylate but not with bromoacrolein.

AB - A chiral titanium complex 1a derived from 6,6'-dibromo-1,1'-bi-2-naphthol is found to give higher endo- and enantioselectivity along with higher catalytic activity than the parent binaphthol-derived titanium complex 1b in the (hetero) Diels-Alder reactions of 1-methoxydienes (2a and 2c) with methacrolein and glyoxylate but not with bromoacrolein.

KW - (hetero) Diels-Alder reaction

KW - asymmetric catalysis

KW - binaphthol

KW - enantioselectivity

KW - Lewis acid

KW - titanium complex

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U2 - 10.1055/s-1995-5138

DO - 10.1055/s-1995-5138

M3 - Article

AN - SCOPUS:0003180189

SN - 0936-5214

VL - 1995

SP - 967

EP - 968

JO - Synlett

JF - Synlett

IS - 9

ER -

Asymmetric catalysis of (Hetero) diels-alder cycloadditions by a modified binaphthol-derived titanium complex

Abstract

Keywords

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