Journal article

Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers.

Abstract:: Organolithium-induced alkylative ring opening of N-sulfonyl-protected aziridinyl ethers is described. The reactions were efficiently carried out with a variety of organolithiums, providing a promising new strategy to unsaturated amino alcohols and ethers. Cis- and trans-1,4-dimethoxybut-2-ene-derived aziridines were prepared, and their propensity to undergo organolithium- induced alkylative desymmetrization is detailed. Use of a single enantiomer of the latter aziridine provides a route to enantiopure unsaturated amino ethers.

Publication status:: Published

Actions

Email

Email this record

Send the bibliographic details of this record to your email address.

Your Email
Please enter the email address that the record information will be sent to.

-
Your message (optional)
Please add any additional information to be included within the email.
Share
Cite

Cite this record

APA Style

Hodgson, D., Stefane, B., Miles, T., & Witherington, J. (2006). Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers. Journal of Organic Chemistry, 71(22), 8510–8515.

MLA Style

Hodgson, D, et al. “Organolithium-Induced Alkylative Ring Opening of Aziridines: Synthesis of Unsaturated Amino Alcohols and Ethers.” Journal of Organic Chemistry, vol. 71, no. 22, 2006, pp. 8510–15.

Chicago Style

Hodgson, D, B Stefane, T Miles, and J Witherington. 2006. “Organolithium-Induced Alkylative Ring Opening of Aziridines: Synthesis of Unsaturated Amino Alcohols and Ethers.” Journal of Organic Chemistry 71 (22): 8510–15.
Print

Access Document

Publisher copy:: 10.1021/jo0615201

Authors

+ Hodgson, D More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Stefane, B More by this author

Role:: Author

+ Miles, T More by this author

Role:: Author

+ Witherington, J More by this author

Role:: Author

Journal:: Journal of organic chemistry More from this journal
Volume:: 71
Issue:: 22
Pages:: 8510-8515
Publication date:: 2006-10-01
DOI:: 10.1021/jo0615201
EISSN:: 1520-6904
ISSN:: 0022-3263

Language:: English
Keywords:: Alkylation

Lithium

Molecular Structure

Organometallic Compounds

Ethers

Stereoisomerism

Amino Alcohols

Aziridines
Pubs id:: pubs:33645
UUID:: uuid:f5ad34e5-cba3-45c1-9da0-a8c030700cb3
Local pid:: pubs:33645
Source identifiers:: 33645
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_f5ad34e5cba345c19da0a8c030700cb3

Terms of use

Copyright date:: 2006

Licence:: Terms and Conditions of Use for Oxford University Research Archive

Views and Downloads

About views and downloads

If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP