Anomalous threo-diastereoselectivity in allylic silane- or stannane-aldehyde condensation reactions: New interpretation of the antiperiplanar vs. synclinal problem on the transition-state conformations

Koichi Mikami; Kazuya Kawamoto; Teck Peng Loh; Takeshi Nakai

doi:10.1039/C39900001161

Anomalous threo-diastereoselectivity in allylic silane- or stannane-aldehyde condensation reactions: New interpretation of the antiperiplanar vs. synclinal problem on the transition-state conformations

Koichi Mikami^*, Kazuya Kawamoto, Teck Peng Loh, Takeshi Nakai

^*Corresponding author for this work

Tokyo Institute of Technology

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

47 Citations (Scopus)

Abstract

Unusual threo-diastereoselectivity has been observed in the intermolecular reactions of β-substituted crotyl-silane or-stannane with 2-benzyloxypropanal under chelation conditions, which implies preference for the synclinal over the antiperiplanar transition state.

Original language	English
Pages (from-to)	1161-1163
Number of pages	3
Journal	Chemical Communications
Issue number	17
DOIs	https://doi.org/10.1039/C39900001161
Publication status	Published - 1990
Externally published	Yes

ASJC Scopus Subject Areas

Molecular Medicine

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10.1039/C39900001161

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title = "Anomalous threo-diastereoselectivity in allylic silane- or stannane-aldehyde condensation reactions: New interpretation of the antiperiplanar vs. synclinal problem on the transition-state conformations",

abstract = "Unusual threo-diastereoselectivity has been observed in the intermolecular reactions of β-substituted crotyl-silane or-stannane with 2-benzyloxypropanal under chelation conditions, which implies preference for the synclinal over the antiperiplanar transition state.",

author = "Koichi Mikami and Kazuya Kawamoto and Loh, {Teck Peng} and Takeshi Nakai",

year = "1990",

doi = "10.1039/C39900001161",

language = "English",

pages = "1161--1163",

journal = "Chemical Communications",

issn = "0022-4936",

publisher = "Royal Society of Chemistry",

number = "17",

}

Anomalous threo-diastereoselectivity in allylic silane- or stannane-aldehyde condensation reactions: New interpretation of the antiperiplanar vs. synclinal problem on the transition-state conformations. / Mikami, Koichi; Kawamoto, Kazuya; Loh, Teck Peng et al.
In: Chemical Communications, No. 17, 1990, p. 1161-1163.

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

TY - JOUR

T1 - Anomalous threo-diastereoselectivity in allylic silane- or stannane-aldehyde condensation reactions

T2 - New interpretation of the antiperiplanar vs. synclinal problem on the transition-state conformations

AU - Mikami, Koichi

AU - Kawamoto, Kazuya

AU - Loh, Teck Peng

AU - Nakai, Takeshi

PY - 1990

Y1 - 1990

N2 - Unusual threo-diastereoselectivity has been observed in the intermolecular reactions of β-substituted crotyl-silane or-stannane with 2-benzyloxypropanal under chelation conditions, which implies preference for the synclinal over the antiperiplanar transition state.

AB - Unusual threo-diastereoselectivity has been observed in the intermolecular reactions of β-substituted crotyl-silane or-stannane with 2-benzyloxypropanal under chelation conditions, which implies preference for the synclinal over the antiperiplanar transition state.

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DO - 10.1039/C39900001161

M3 - Article

AN - SCOPUS:37049067086

SN - 0022-4936

SP - 1161

EP - 1163

JO - Chemical Communications

JF - Chemical Communications

IS - 17

ER -

Anomalous threo-diastereoselectivity in allylic silane- or stannane-aldehyde condensation reactions: New interpretation of the antiperiplanar vs. synclinal problem on the transition-state conformations

Abstract

ASJC Scopus Subject Areas

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