Dearomatizing disrotatory electrocyclic ring closure of lithiated N-benzoyloxazolidines

Jonathan Clayden; Savroop Purewal; Madeleine Helliwell; Simon J. Mantell

doi:10.1002/1521-3773(20020315)41:6<1049::AID-ANIE1049>3.0.CO;2-7

Dearomatizing disrotatory electrocyclic ring closure of lithiated N-benzoyloxazolidines

Jonathan Clayden
, Savroop Purewal
, Madeleine Helliwell
, Simon J. Mantell

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

Abstract

Loss of aromaticity ensues when N-benzoyl oxazolidines are lithiated and undergo a 6π disrotatory electrocyclization (see scheme). The stereochemistry of the cyclization shows it to be a new example of an electrocyclic ring closure. The cis-tricyclic products epimerize to their more stable trans diastereoisomers in aqueous acid.

Original language	English
Pages (from-to)	1049-1051
Number of pages	2
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	6
DOIs	https://doi.org/10.1002/1521-3773(20020315)41:6<1049::AID-ANIE1049>3.0.CO;2-7
Publication status	Published - 15 Mar 2002

Keywords

Amides
Cyclization
Lithiation
Pericyclic reaction
Stereoselectivity

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10.1002/1521-3773(20020315)41:6<1049::AID-ANIE1049>3.0.CO;2-7

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title = "Dearomatizing disrotatory electrocyclic ring closure of lithiated N-benzoyloxazolidines",

abstract = "Loss of aromaticity ensues when N-benzoyl oxazolidines are lithiated and undergo a 6π disrotatory electrocyclization (see scheme). The stereochemistry of the cyclization shows it to be a new example of an electrocyclic ring closure. The cis-tricyclic products epimerize to their more stable trans diastereoisomers in aqueous acid.",

keywords = "Amides, Cyclization, Lithiation, Pericyclic reaction, Stereoselectivity",

author = "Jonathan Clayden and Savroop Purewal and Madeleine Helliwell and Mantell, \{Simon J.\}",

year = "2002",

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T1 - Dearomatizing disrotatory electrocyclic ring closure of lithiated N-benzoyloxazolidines

AU - Clayden, Jonathan

AU - Purewal, Savroop

AU - Helliwell, Madeleine

AU - Mantell, Simon J.

PY - 2002/3/15

Y1 - 2002/3/15

N2 - Loss of aromaticity ensues when N-benzoyl oxazolidines are lithiated and undergo a 6π disrotatory electrocyclization (see scheme). The stereochemistry of the cyclization shows it to be a new example of an electrocyclic ring closure. The cis-tricyclic products epimerize to their more stable trans diastereoisomers in aqueous acid.

AB - Loss of aromaticity ensues when N-benzoyl oxazolidines are lithiated and undergo a 6π disrotatory electrocyclization (see scheme). The stereochemistry of the cyclization shows it to be a new example of an electrocyclic ring closure. The cis-tricyclic products epimerize to their more stable trans diastereoisomers in aqueous acid.

KW - Amides

KW - Cyclization

KW - Lithiation

KW - Pericyclic reaction

KW - Stereoselectivity

U2 - 10.1002/1521-3773(20020315)41:6<1049::AID-ANIE1049>3.0.CO;2-7

DO - 10.1002/1521-3773(20020315)41:6<1049::AID-ANIE1049>3.0.CO;2-7

M3 - Article

SN - 1433-7851

VL - 41

SP - 1049

EP - 1051

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

Dearomatizing disrotatory electrocyclic ring closure of lithiated N-benzoyloxazolidines

Abstract

Keywords

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