Chirality transfer in palladium catalyzed reactions of allylammonium salts

Takayuki Doi; Arata Yanagisawa; Masahiro Miyazawa; Keiji Yamamoto

doi:10.1016/0957-4166(95)00021-G

Chirality transfer in palladium catalyzed reactions of allylammonium salts

Takayuki Doi^*, Arata Yanagisawa, Masahiro Miyazawa, Keiji Yamamoto

^*Corresponding author for this work

Department of Chemistry

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

31 Scopus citations

Abstract

Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst. The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration due probably to a prior isomerization from anti to syn-π-allylpalladium intermediate (14→15). The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.

Original language	English
Pages (from-to)	389-392
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	6
Issue number	2
DOIs	https://doi.org/10.1016/0957-4166(95)00021-G
State	Published - 1995/02

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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@article{0e1e2f9035844c628fe00af03ebd579b,

title = "Chirality transfer in palladium catalyzed reactions of allylammonium salts",

abstract = "Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst. The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration due probably to a prior isomerization from anti to syn-π-allylpalladium intermediate (14→15). The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.",

author = "Takayuki Doi and Arata Yanagisawa and Masahiro Miyazawa and Keiji Yamamoto",

note = "Funding Information: ACKNOWLEDGMENT. Support by the Grant-in-Aid for Genenal Scientific Research (No. 0440301) from the Ministry of Education, Science, and Culture is gratefully acknowledged.",

year = "1995",

month = feb,

doi = "10.1016/0957-4166(95)00021-G",

language = "英語",

volume = "6",

pages = "389--392",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Ltd.",

number = "2",

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TY - JOUR

T1 - Chirality transfer in palladium catalyzed reactions of allylammonium salts

AU - Doi, Takayuki

AU - Yanagisawa, Arata

AU - Miyazawa, Masahiro

AU - Yamamoto, Keiji

N1 - Funding Information: ACKNOWLEDGMENT. Support by the Grant-in-Aid for Genenal Scientific Research (No. 0440301) from the Ministry of Education, Science, and Culture is gratefully acknowledged.

PY - 1995/2

Y1 - 1995/2

N2 - Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst. The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration due probably to a prior isomerization from anti to syn-π-allylpalladium intermediate (14→15). The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.

AB - Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst. The reaction proceeded predominantly with 1,3 transposition and with inversion of configuration due probably to a prior isomerization from anti to syn-π-allylpalladium intermediate (14→15). The stereochemistry observed in the reaction with phenylzinc chloride was opposite to that with the soft nucleophile.

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U2 - 10.1016/0957-4166(95)00021-G

DO - 10.1016/0957-4166(95)00021-G

M3 - 学術論文

AN - SCOPUS:0028921695

SN - 0957-4166

VL - 6

SP - 389

EP - 392

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 2

ER -

Chirality transfer in palladium catalyzed reactions of allylammonium salts

Abstract

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