Enantio- and diastereoselective catalysis of addition reaction of allylic silanes and stannanes to glyoxylates by binaphthol-derived titanium complex

Seiichi Aoki; Koichi Mikami; Masahiro Terada; Takeshi Nakai

doi:10.1016/S0040-4020(01)80535-4

Enantio- and diastereoselective catalysis of addition reaction of allylic silanes and stannanes to glyoxylates by binaphthol-derived titanium complex

Seiichi Aoki, Koichi Mikami, Masahiro Terada, Takeshi Nakai

SCI - Chemistry

Tokyo Institute of Technology

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

124 Citations (Scopus)

Abstract

Chiral titanium complex (1), prepared in situ from optically pure binaphthol and diisopropoxytitanium dihalide in the presence of molecular sieves, is shown to catalyze the addition reactions of crotylsilanes and -stannanes to glyoxylates to afford (syn)-α-hydroxy-β-methyl esters in highly scalemic forms with high diastereoselectivity.

Original language	English
Pages (from-to)	1783-1792
Number of pages	10
Journal	Tetrahedron
Volume	49
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4020(01)80535-4
Publication status	Published - 1993 Feb 26

Keywords

Allylic silane
Allylic stannane
Asymmetric catalysis
Binaphthol-derived titanium dihalide
Carbonyl-addition reaction
Carbonyl-ene reaction
Chiral titanium complex
Diastereocontrol
Enantiocontrol
Glyoxylate

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10.1016/S0040-4020(01)80535-4

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title = "Enantio- and diastereoselective catalysis of addition reaction of allylic silanes and stannanes to glyoxylates by binaphthol-derived titanium complex",

abstract = "Chiral titanium complex (1), prepared in situ from optically pure binaphthol and diisopropoxytitanium dihalide in the presence of molecular sieves, is shown to catalyze the addition reactions of crotylsilanes and -stannanes to glyoxylates to afford (syn)-α-hydroxy-β-methyl esters in highly scalemic forms with high diastereoselectivity.",

keywords = "Allylic silane, Allylic stannane, Asymmetric catalysis, Binaphthol-derived titanium dihalide, Carbonyl-addition reaction, Carbonyl-ene reaction, Chiral titanium complex, Diastereocontrol, Enantiocontrol, Glyoxylate",

author = "Seiichi Aoki and Koichi Mikami and Masahiro Terada and Takeshi Nakai",

year = "1993",

month = feb,

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doi = "10.1016/S0040-4020(01)80535-4",

language = "English",

volume = "49",

pages = "1783--1792",

journal = "Tetrahedron",

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T1 - Enantio- and diastereoselective catalysis of addition reaction of allylic silanes and stannanes to glyoxylates by binaphthol-derived titanium complex

AU - Aoki, Seiichi

AU - Mikami, Koichi

AU - Terada, Masahiro

AU - Nakai, Takeshi

PY - 1993/2/26

Y1 - 1993/2/26

N2 - Chiral titanium complex (1), prepared in situ from optically pure binaphthol and diisopropoxytitanium dihalide in the presence of molecular sieves, is shown to catalyze the addition reactions of crotylsilanes and -stannanes to glyoxylates to afford (syn)-α-hydroxy-β-methyl esters in highly scalemic forms with high diastereoselectivity.

AB - Chiral titanium complex (1), prepared in situ from optically pure binaphthol and diisopropoxytitanium dihalide in the presence of molecular sieves, is shown to catalyze the addition reactions of crotylsilanes and -stannanes to glyoxylates to afford (syn)-α-hydroxy-β-methyl esters in highly scalemic forms with high diastereoselectivity.

KW - Allylic silane

KW - Allylic stannane

KW - Asymmetric catalysis

KW - Binaphthol-derived titanium dihalide

KW - Carbonyl-addition reaction

KW - Carbonyl-ene reaction

KW - Chiral titanium complex

KW - Diastereocontrol

KW - Enantiocontrol

KW - Glyoxylate

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U2 - 10.1016/S0040-4020(01)80535-4

DO - 10.1016/S0040-4020(01)80535-4

M3 - Article

AN - SCOPUS:0027446533

SN - 0040-4020

VL - 49

SP - 1783

EP - 1792

JO - Tetrahedron

JF - Tetrahedron

IS - 9

ER -

Enantio- and diastereoselective catalysis of addition reaction of allylic silanes and stannanes to glyoxylates by binaphthol-derived titanium complex

Abstract

Keywords

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