Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines

David M Hodgson; Christopher I Pearson; Madiha Kazmi

doi:10.1021/ol403626k

Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines

Org Lett. 2014 Feb 7;16(3):856-9. doi: 10.1021/ol403626k. Epub 2014 Jan 10.

Authors

David M Hodgson¹, Christopher I Pearson, Madiha Kazmi

Affiliation

¹ Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford OX1 3TA, U.K.

Abstract

s-BuLi-induced α-lithiation-elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ α-lithiation generates N-Boc-2-lithio-2-azetine which can be trapped with electrophiles, either directly (carbonyl or heteroatom electrophiles) or after transmetalation to copper (allowing allylations and propargylations), providing a concise access to 2-substituted 2-azetines.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Azetines / chemical synthesis*
Azetines / chemistry*
Copper / chemistry
Lithium / chemistry*
Molecular Structure
Organometallic Compounds / chemical synthesis*
Organometallic Compounds / chemistry*
Stereoisomerism

Substances

Azetines
N-Boc-2-lithio-2-azetine
Organometallic Compounds
Copper
Lithium