Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives

δ-borylated amides

G. L. Hoang, S. Zhang, James M Takacs

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

γ,δ-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed δ-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the γ-borylation of γ,δ-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal in the sense of π-facial selectivity.

Original languageEnglish (US)
Pages (from-to)4838-4841
Number of pages4
JournalChemical Communications
Volume54
Issue number38
DOIs
StatePublished - Jan 1 2018

Fingerprint

Rhodium
Alkenes
Amides
Olefins
Derivatives
Esters
4,4,5,5-tetramethyl(1,3,2)dioxaborolane

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives : δ-borylated amides. / Hoang, G. L.; Zhang, S.; Takacs, James M.

In: Chemical Communications, Vol. 54, No. 38, 01.01.2018, p. 4838-4841.

Research output: Contribution to journalArticle

@article{cab9bf891f63433886befeb6d5e8ccab,
title = "Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides",
abstract = "γ,δ-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed δ-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the γ-borylation of γ,δ-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal in the sense of π-facial selectivity.",
author = "Hoang, {G. L.} and S. Zhang and Takacs, {James M}",
year = "2018",
month = "1",
day = "1",
doi = "10.1039/c8cc01563e",
language = "English (US)",
volume = "54",
pages = "4838--4841",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "38",

}

TY - JOUR

T1 - Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives

T2 - δ-borylated amides

AU - Hoang, G. L.

AU - Zhang, S.

AU - Takacs, James M

PY - 2018/1/1

Y1 - 2018/1/1

N2 - γ,δ-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed δ-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the γ-borylation of γ,δ-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal in the sense of π-facial selectivity.

AB - γ,δ-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed δ-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the γ-borylation of γ,δ-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal in the sense of π-facial selectivity.

UR - http://www.scopus.com/inward/record.url?scp=85046867396&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85046867396&partnerID=8YFLogxK

U2 - 10.1039/c8cc01563e

DO - 10.1039/c8cc01563e

M3 - Article

VL - 54

SP - 4838

EP - 4841

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 38

ER -