Borinic Acid/Halide Co-catalyzed Semipinacol Rearrangements
of 2,3-Epoxy Alcohols
Version 2 2018-08-15, 20:49
Version 1 2018-08-15, 20:48
Posted on 2018-08-15 - 20:49
A new mode of catalysis of the semipinacol
rearrangement of 2,3-epoxy
alcohols is described. In combination with a halide salt additive,
diarylborinic acids promote a Type II rearrangement that occurs with
net retention of configuration. This unusual stereochemical outcome
is consistent with a mechanism involving regioselective ring opening
of the epoxy alcohol by halide, followed by rearrangement of the resulting
halohydrin-derived borinic ester. The protocol is applicable to a
range of substrates, enabling ring contractions and expansions as
well as stereospecific syntheses of acyclic β-hydroxycarbonyl
compounds.
CITE THIS COLLECTION
DataCite
3 Biotech
3D Printing in Medicine
3D Research
3D-Printed Materials and Systems
4OR
AAPG Bulletin
AAPS Open
AAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)
Academic Medicine
Academic Pediatrics
Academic Psychiatry
Academic Questions
Academy of Management Discoveries
Academy of Management Journal
Academy of Management Learning and Education
Academy of Management Perspectives
Academy of Management Proceedings
Academy of Management Review
Tanveer, Kashif; Kim, Seung-Joon; Taylor, Mark S. (2018). Borinic Acid/Halide Co-catalyzed Semipinacol Rearrangements
of 2,3-Epoxy Alcohols. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b02248
or
Select your citation style and then place your mouse over the citation text to select it.
SHARE
Usage metrics
Read the peer-reviewed publication
AUTHORS (3)
KT
Kashif Tanveer
SK
Seung-Joon Kim
MT
Mark S. Taylor