Diastereocontrol in Lewis acid-catalyzed Michael reactions of 4-siloxycyclopentenone with ketene silyl acetals: Stereoelectronic vs. steric effect

Junzo Otera; Yukihiro Fujita; Shunichi Fukuzumi; Kei ichi Hirai; Jin Hua Gu; Takeshi Nakai

doi:10.1016/0040-4039(94)02174-A

Diastereocontrol in Lewis acid-catalyzed Michael reactions of 4-siloxycyclopentenone with ketene silyl acetals: Stereoelectronic vs. steric effect

Junzo Otera, Yukihiro Fujita, Shunichi Fukuzumi, Kei ichi Hirai, Jin Hua Gu, Takeshi Nakai

Department of Chemistry & Nanoscience

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

22 Scopus citations

Abstract

The title reactions are shown to proceed with sterically unfavorable syn preference (to the siloxy group) when steric demand of the acetals is trivial, whereas β-substitution of acetals results in reversal of diastereoselection. These results are discussed in terms of the stereoelectronic vs. steric effect.

Original language	English
Pages (from-to)	95-98
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	1
DOIs	https://doi.org/10.1016/0040-4039(94)02174-A
State	Published - 2 Jan 1995

Access to Document

10.1016/0040-4039(94)02174-A

Cite this

@article{1b1d26d642c5474c8ba00a8af0644ba7,

title = "Diastereocontrol in Lewis acid-catalyzed Michael reactions of 4-siloxycyclopentenone with ketene silyl acetals: Stereoelectronic vs. steric effect",

abstract = "The title reactions are shown to proceed with sterically unfavorable syn preference (to the siloxy group) when steric demand of the acetals is trivial, whereas β-substitution of acetals results in reversal of diastereoselection. These results are discussed in terms of the stereoelectronic vs. steric effect.",

author = "Junzo Otera and Yukihiro Fujita and Shunichi Fukuzumi and Hirai, {Kei ichi} and Gu, {Jin Hua} and Takeshi Nakai",

year = "1995",

month = jan,

day = "2",

doi = "10.1016/0040-4039(94)02174-A",

language = "English",

volume = "36",

pages = "95--98",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "1",

}

TY - JOUR

T1 - Diastereocontrol in Lewis acid-catalyzed Michael reactions of 4-siloxycyclopentenone with ketene silyl acetals

T2 - Stereoelectronic vs. steric effect

AU - Otera, Junzo

AU - Fujita, Yukihiro

AU - Fukuzumi, Shunichi

AU - Hirai, Kei ichi

AU - Gu, Jin Hua

AU - Nakai, Takeshi

PY - 1995/1/2

Y1 - 1995/1/2

N2 - The title reactions are shown to proceed with sterically unfavorable syn preference (to the siloxy group) when steric demand of the acetals is trivial, whereas β-substitution of acetals results in reversal of diastereoselection. These results are discussed in terms of the stereoelectronic vs. steric effect.

AB - The title reactions are shown to proceed with sterically unfavorable syn preference (to the siloxy group) when steric demand of the acetals is trivial, whereas β-substitution of acetals results in reversal of diastereoselection. These results are discussed in terms of the stereoelectronic vs. steric effect.

UR - http://www.scopus.com/inward/record.url?scp=0028854518&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(94)02174-A

DO - 10.1016/0040-4039(94)02174-A

M3 - Article

AN - SCOPUS:0028854518

SN - 0040-4039

VL - 36

SP - 95

EP - 98

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

Diastereocontrol in Lewis acid-catalyzed Michael reactions of 4-siloxycyclopentenone with ketene silyl acetals: Stereoelectronic vs. steric effect

Abstract

Access to Document

Fingerprint

Cite this