Synthesis of chiral dendrimers with a hydrocarbon backbone and application to the catalytic enantioselective addition of dialkylzincs to aldehydes

Itaru Sato; Takanori Shibata; Koji Ohtake; Ryo Kodaka; Yutaka Hirokawa; Nobuaki Shirai; Kenso Soai

doi:10.1016/S0040-4039(00)00365-8

Synthesis of chiral dendrimers with a hydrocarbon backbone and application to the catalytic enantioselective addition of dialkylzincs to aldehydes

Itaru Sato, Takanori Shibata, Koji Ohtake, Ryo Kodaka, Yutaka Hirokawa, Nobuaki Shirai, Kenso Soai^*

^*Corresponding author for this work

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

56 Citations (Scopus)

Abstract

Chiral dendrimers with three or six β-amino alcohols on hyperbranched hydrocarbon chain-ends were synthesized. These macromolecules can act as chiral catalysts for the enantioselective addition of dialkylzincs to aldehydes. The corresponding secondary alcohols are obtained in high enantiomeric excess (up to 86% e.e.). (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	3123-3126
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(00)00365-8
Publication status	Published - 2000 Apr 22
Externally published	Yes

Keywords

Asymmetric synthesis
Catalysts
Dendrimers
Enantioselection

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)00365-8

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title = "Synthesis of chiral dendrimers with a hydrocarbon backbone and application to the catalytic enantioselective addition of dialkylzincs to aldehydes",

abstract = "Chiral dendrimers with three or six β-amino alcohols on hyperbranched hydrocarbon chain-ends were synthesized. These macromolecules can act as chiral catalysts for the enantioselective addition of dialkylzincs to aldehydes. The corresponding secondary alcohols are obtained in high enantiomeric excess (up to 86% e.e.). (C) 2000 Elsevier Science Ltd.",

keywords = "Asymmetric synthesis, Catalysts, Dendrimers, Enantioselection",

author = "Itaru Sato and Takanori Shibata and Koji Ohtake and Ryo Kodaka and Yutaka Hirokawa and Nobuaki Shirai and Kenso Soai",

note = "Funding Information: We thank Professors James D. Wuest at the Universit{\'e} de Montr{\'e}al and Peter J. Stang at the University of Utah for information on the preparation of compound 5 and ethynylbenzene, respectively. Partial financial support from the Ministry of Education, Science, Sports and Culture, Japan is gratefully acknowledged.",

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doi = "10.1016/S0040-4039(00)00365-8",

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pages = "3123--3126",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of chiral dendrimers with a hydrocarbon backbone and application to the catalytic enantioselective addition of dialkylzincs to aldehydes

AU - Sato, Itaru

AU - Shibata, Takanori

AU - Ohtake, Koji

AU - Kodaka, Ryo

AU - Hirokawa, Yutaka

AU - Shirai, Nobuaki

AU - Soai, Kenso

N1 - Funding Information: We thank Professors James D. Wuest at the Université de Montréal and Peter J. Stang at the University of Utah for information on the preparation of compound 5 and ethynylbenzene, respectively. Partial financial support from the Ministry of Education, Science, Sports and Culture, Japan is gratefully acknowledged.

PY - 2000/4/22

Y1 - 2000/4/22

N2 - Chiral dendrimers with three or six β-amino alcohols on hyperbranched hydrocarbon chain-ends were synthesized. These macromolecules can act as chiral catalysts for the enantioselective addition of dialkylzincs to aldehydes. The corresponding secondary alcohols are obtained in high enantiomeric excess (up to 86% e.e.). (C) 2000 Elsevier Science Ltd.

AB - Chiral dendrimers with three or six β-amino alcohols on hyperbranched hydrocarbon chain-ends were synthesized. These macromolecules can act as chiral catalysts for the enantioselective addition of dialkylzincs to aldehydes. The corresponding secondary alcohols are obtained in high enantiomeric excess (up to 86% e.e.). (C) 2000 Elsevier Science Ltd.

KW - Asymmetric synthesis

KW - Catalysts

KW - Dendrimers

KW - Enantioselection

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DO - 10.1016/S0040-4039(00)00365-8

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SN - 0040-4039

VL - 41

SP - 3123

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

Synthesis of chiral dendrimers with a hydrocarbon backbone and application to the catalytic enantioselective addition of dialkylzincs to aldehydes

Abstract

Keywords

ASJC Scopus subject areas

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