Asymmetric synthesis of β-lactams. I. The reaction of dimethylketene silyl acetal with (S)-alkylidene(1-arylethyl)amines promoted by titanium tetrachloride

Iwao Ojima; Shin ichi Inaba

doi:10.1016/S0040-4039(00)71491-2

Asymmetric synthesis of β-lactams. I. The reaction of dimethylketene silyl acetal with (S)-alkylidene(1-arylethyl)amines promoted by titanium tetrachloride

Iwao Ojima
, Shin ichi Inaba

Chemistry

Sagami Chemical Research Institute

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

65 Scopus citations

Abstract

Asymmetric synthesis of β-lactams by means of the reaction of dimethylketene silyl acetal with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride was studied. The extent of the asymmetric induction was in the range of 44-78% (diastereomeric purity 72-89%) and the (S)-configuration was turned to be preferentially induced at the ⁴C position of the resulting β-lactams.

Original language	English
Pages (from-to)	2077-2080
Number of pages	4
Journal	Tetrahedron Letters
Volume	21
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(00)71491-2
State	Published - 1980

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title = "Asymmetric synthesis of β-lactams. I. The reaction of dimethylketene silyl acetal with (S)-alkylidene(1-arylethyl)amines promoted by titanium tetrachloride",

abstract = "Asymmetric synthesis of β-lactams by means of the reaction of dimethylketene silyl acetal with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride was studied. The extent of the asymmetric induction was in the range of 44-78\% (diastereomeric purity 72-89\%) and the (S)-configuration was turned to be preferentially induced at the 4C position of the resulting β-lactams.",

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AU - Inaba, Shin ichi

PY - 1980

Y1 - 1980

N2 - Asymmetric synthesis of β-lactams by means of the reaction of dimethylketene silyl acetal with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride was studied. The extent of the asymmetric induction was in the range of 44-78% (diastereomeric purity 72-89%) and the (S)-configuration was turned to be preferentially induced at the 4C position of the resulting β-lactams.

AB - Asymmetric synthesis of β-lactams by means of the reaction of dimethylketene silyl acetal with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride was studied. The extent of the asymmetric induction was in the range of 44-78% (diastereomeric purity 72-89%) and the (S)-configuration was turned to be preferentially induced at the 4C position of the resulting β-lactams.

UR - https://www.scopus.com/pages/publications/0001673653

U2 - 10.1016/S0040-4039(00)71491-2

DO - 10.1016/S0040-4039(00)71491-2

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ER -

Asymmetric synthesis of β-lactams. I. The reaction of dimethylketene silyl acetal with (S)-alkylidene(1-arylethyl)amines promoted by titanium tetrachloride

Abstract

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