Asymmetric synthesis of β-lactams. II. Highly effective asymmetric induction by means of "titanium template"

Iwao Ojima; Shin ichi Inaba

doi:10.1016/S0040-4039(00)71492-4

Asymmetric synthesis of β-lactams. II. Highly effective asymmetric induction by means of "titanium template"

Iwao Ojima
, Shin ichi Inaba

Chemistry

Stony Brook University

Sagami Chemical Research Institute

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

63 Scopus citations

Abstract

The reaction of dimethylketene methyl trimethylsilyl acetal with the Schiff bases of chiral α-amino esters in the presence of titanium tetrachloride gave the corresponding β-lactams with extremely high stereoselectivity (up to > 99% diastereomeric purity). Possible mechanism for the highly effective asymmetric induction using "titanium template" is proposed.

Original language	English
Pages (from-to)	2081-2084
Number of pages	4
Journal	Tetrahedron Letters
Volume	21
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(00)71492-4
State	Published - 1980

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10.1016/S0040-4039(00)71492-4

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title = "Asymmetric synthesis of β-lactams. II. Highly effective asymmetric induction by means of {"}titanium template{"}",

abstract = "The reaction of dimethylketene methyl trimethylsilyl acetal with the Schiff bases of chiral α-amino esters in the presence of titanium tetrachloride gave the corresponding β-lactams with extremely high stereoselectivity (up to > 99\% diastereomeric purity). Possible mechanism for the highly effective asymmetric induction using {"}titanium template{"} is proposed.",

author = "Iwao Ojima and Inaba, \{Shin ichi\}",

year = "1980",

doi = "10.1016/S0040-4039(00)71492-4",

language = "English",

volume = "21",

pages = "2081--2084",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Asymmetric synthesis of β-lactams. II. Highly effective asymmetric induction by means of "titanium template"

AU - Ojima, Iwao

AU - Inaba, Shin ichi

PY - 1980

Y1 - 1980

N2 - The reaction of dimethylketene methyl trimethylsilyl acetal with the Schiff bases of chiral α-amino esters in the presence of titanium tetrachloride gave the corresponding β-lactams with extremely high stereoselectivity (up to > 99% diastereomeric purity). Possible mechanism for the highly effective asymmetric induction using "titanium template" is proposed.

AB - The reaction of dimethylketene methyl trimethylsilyl acetal with the Schiff bases of chiral α-amino esters in the presence of titanium tetrachloride gave the corresponding β-lactams with extremely high stereoselectivity (up to > 99% diastereomeric purity). Possible mechanism for the highly effective asymmetric induction using "titanium template" is proposed.

UR - https://www.scopus.com/pages/publications/0001705805

U2 - 10.1016/S0040-4039(00)71492-4

DO - 10.1016/S0040-4039(00)71492-4

M3 - Article

SN - 0040-4039

VL - 21

SP - 2081

EP - 2084

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

Asymmetric synthesis of β-lactams. II. Highly effective asymmetric induction by means of "titanium template"

Abstract

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