Formal [4 + 2] cycloaddition of alkoxy-substituted donor-acceptor cyclobutanes and aldehydes catalyzed by Yb(OTf)3

Mahmoud M Abd Rabo Moustafa; Andrew C Stevens; Ben P Machin; Brian L Pagenkopf

doi:10.1021/ol102063f

Formal [4 + 2] cycloaddition of alkoxy-substituted donor-acceptor cyclobutanes and aldehydes catalyzed by Yb(OTf)3

Org Lett. 2010 Nov 5;12(21):4736-8. doi: 10.1021/ol102063f.

Authors

Mahmoud M Abd Rabo Moustafa¹, Andrew C Stevens, Ben P Machin, Brian L Pagenkopf

Affiliation

¹ Department of Chemistry, The University of Western Ontario, 1151 Richmond Street, London, Ontario N6A 5B7, Canada.

PMID: 20925408
DOI: 10.1021/ol102063f

Abstract

The cycloaddition between 2-alkoxy-1,1-cyclobutane diesters and aromatic, heteroaromatic, or aliphatic aldehydes under Yb(OTf)(3) catalysis generates tetrahydropyrans in high yields with exclusive cis-stereochemistry.

Publication types

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

MeSH terms

Alcohols / chemistry*
Aldehydes / chemistry*
Catalysis
Cyclization
Cyclobutanes / chemistry*
Mesylates / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*

Substances

Alcohols
Aldehydes
Cyclobutanes
Mesylates
Organometallic Compounds
alkoxyl radical
ytterbium(III) triflate