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

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

21 Citations (Scopus)

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	3
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

Research Groups and Themes

Organic & Biological

Keywords

Amides
Cyclization
Lithiation
Pericyclic reaction
Stereoselectivity

Access to Document

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

Handle.net

Persistent link

Cite this

@article{6a57af764f804f58954a15716f59e9af,

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",

month = mar,

day = "15",

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

language = "English",

volume = "41",

pages = "1049--1051",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley \& Sons, Ltd.",

number = "6",

}

TY - JOUR

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

UR - https://www.scopus.com/pages/publications/0037087565

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 (Academic Journal)

AN - SCOPUS:0037087565

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

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

Cite this