Double stereocontrol in α-alkylation of chiral lithium dienolates generated from (E)-α,β-olefinic amides and esters

Katsuhiko Tomooka; Atsushi Nagasawa; Takeshi Nakai

doi:10.1246/cl.1998.1049

Double stereocontrol in α-alkylation of chiral lithium dienolates generated from (E)-α,β-olefinic amides and esters

Katsuhiko Tomooka, Atsushi Nagasawa, Takeshi Nakai

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

16 Citations (Scopus)

Abstract

The methylation of the lithium dienolate generated from (E)-α,β-olefinic amide with Katsuki's chiral auxiliary affords the α-methylated β,γ-enamide in an exceptionally high Z-selectivity (99%) over the terminal olefinic bond along with 99% de at the α-chiral center. The origin of the high Z-selectivity is discussed.

Original language	English
Pages (from-to)	1049-1050
Number of pages	2
Journal	Chemistry Letters
Issue number	10
DOIs	https://doi.org/10.1246/cl.1998.1049
Publication status	Published - 1998
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.1998.1049

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title = "Double stereocontrol in α-alkylation of chiral lithium dienolates generated from (E)-α,β-olefinic amides and esters",

abstract = "The methylation of the lithium dienolate generated from (E)-α,β-olefinic amide with Katsuki's chiral auxiliary affords the α-methylated β,γ-enamide in an exceptionally high Z-selectivity (99%) over the terminal olefinic bond along with 99% de at the α-chiral center. The origin of the high Z-selectivity is discussed.",

author = "Katsuhiko Tomooka and Atsushi Nagasawa and Takeshi Nakai",

year = "1998",

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T1 - Double stereocontrol in α-alkylation of chiral lithium dienolates generated from (E)-α,β-olefinic amides and esters

AU - Tomooka, Katsuhiko

AU - Nagasawa, Atsushi

AU - Nakai, Takeshi

PY - 1998

Y1 - 1998

N2 - The methylation of the lithium dienolate generated from (E)-α,β-olefinic amide with Katsuki's chiral auxiliary affords the α-methylated β,γ-enamide in an exceptionally high Z-selectivity (99%) over the terminal olefinic bond along with 99% de at the α-chiral center. The origin of the high Z-selectivity is discussed.

AB - The methylation of the lithium dienolate generated from (E)-α,β-olefinic amide with Katsuki's chiral auxiliary affords the α-methylated β,γ-enamide in an exceptionally high Z-selectivity (99%) over the terminal olefinic bond along with 99% de at the α-chiral center. The origin of the high Z-selectivity is discussed.

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DO - 10.1246/cl.1998.1049

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JO - Chemistry Letters

JF - Chemistry Letters

IS - 10

ER -

Double stereocontrol in α-alkylation of chiral lithium dienolates generated from (E)-α,β-olefinic amides and esters

Abstract

All Science Journal Classification (ASJC) codes

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