Stereoselective synthesis of hexahydroindoles and octahydrocyclohepta[b]pyrroles via gold(I)-catalyzed intramolecular 1,4-hydroamination of cyclic 1,3-dienes

Ming-Chang P. Yeh, Hui Fen Pai, Zao Jun Lin, Bo Ren Lee

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

The gold(I)-catalyzed intramolecular hydroamination of cyclohexa-1,3-dienes bearing an arylsulfonamide at the C-5 position proceeds in a 1,4-addition manner to afford hexahydroindole derivatives in a diastereoselective fashion and in good yields, whereas octahydrocyclohepta[b]pyrrole derivatives can be obtained from seven-membered ring substrates under the same reaction conditions. Coordination of the gold(I) species to the 1,3-diene at the double bond adjacent to the arylsulfonamide tether gave an η2-alkene gold complex. The anti-attack of the sulfonamide to the η2-alkene gold complex at the terminal position of the 1,3-diene resulted in the formation of the fused bicyclic ring with a newly formed Au-C bond at the allylic position. Allylic rearrangement of the η1-allylgold complex followed by protodemetalation provided the fused heterobicyclic skeletons and regenerated the catalyst.

Original languageEnglish
Pages (from-to)4789-4794
Number of pages6
JournalTetrahedron
Volume65
Issue number25
DOIs
Publication statusPublished - 2009 Jun 20

Fingerprint

Pyrroles
Gold
Alkenes
Bearings (structural)
Derivatives
Sulfonamides
Skeleton
Catalysts
Substrates

Keywords

  • Cycloheptadiene
  • Cyclohexadiene
  • Gold-catalyzed
  • Hexahydroindoles
  • Hydroamination
  • Intramolecular
  • Octahydrocyclohepta[b]pyrroles
  • Sulfonamide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Stereoselective synthesis of hexahydroindoles and octahydrocyclohepta[b]pyrroles via gold(I)-catalyzed intramolecular 1,4-hydroamination of cyclic 1,3-dienes. / Yeh, Ming-Chang P.; Pai, Hui Fen; Lin, Zao Jun; Lee, Bo Ren.

In: Tetrahedron, Vol. 65, No. 25, 20.06.2009, p. 4789-4794.

Research output: Contribution to journalArticle

@article{b90dcd444ccc4e3f8cdb1ad5f22a1152,
title = "Stereoselective synthesis of hexahydroindoles and octahydrocyclohepta[b]pyrroles via gold(I)-catalyzed intramolecular 1,4-hydroamination of cyclic 1,3-dienes",
abstract = "The gold(I)-catalyzed intramolecular hydroamination of cyclohexa-1,3-dienes bearing an arylsulfonamide at the C-5 position proceeds in a 1,4-addition manner to afford hexahydroindole derivatives in a diastereoselective fashion and in good yields, whereas octahydrocyclohepta[b]pyrrole derivatives can be obtained from seven-membered ring substrates under the same reaction conditions. Coordination of the gold(I) species to the 1,3-diene at the double bond adjacent to the arylsulfonamide tether gave an η2-alkene gold complex. The anti-attack of the sulfonamide to the η2-alkene gold complex at the terminal position of the 1,3-diene resulted in the formation of the fused bicyclic ring with a newly formed Au-C bond at the allylic position. Allylic rearrangement of the η1-allylgold complex followed by protodemetalation provided the fused heterobicyclic skeletons and regenerated the catalyst.",
keywords = "Cycloheptadiene, Cyclohexadiene, Gold-catalyzed, Hexahydroindoles, Hydroamination, Intramolecular, Octahydrocyclohepta[b]pyrroles, Sulfonamide",
author = "Yeh, {Ming-Chang P.} and Pai, {Hui Fen} and Lin, {Zao Jun} and Lee, {Bo Ren}",
year = "2009",
month = "6",
day = "20",
doi = "10.1016/j.tet.2009.04.064",
language = "English",
volume = "65",
pages = "4789--4794",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "25",

}

TY - JOUR

T1 - Stereoselective synthesis of hexahydroindoles and octahydrocyclohepta[b]pyrroles via gold(I)-catalyzed intramolecular 1,4-hydroamination of cyclic 1,3-dienes

AU - Yeh, Ming-Chang P.

AU - Pai, Hui Fen

AU - Lin, Zao Jun

AU - Lee, Bo Ren

PY - 2009/6/20

Y1 - 2009/6/20

N2 - The gold(I)-catalyzed intramolecular hydroamination of cyclohexa-1,3-dienes bearing an arylsulfonamide at the C-5 position proceeds in a 1,4-addition manner to afford hexahydroindole derivatives in a diastereoselective fashion and in good yields, whereas octahydrocyclohepta[b]pyrrole derivatives can be obtained from seven-membered ring substrates under the same reaction conditions. Coordination of the gold(I) species to the 1,3-diene at the double bond adjacent to the arylsulfonamide tether gave an η2-alkene gold complex. The anti-attack of the sulfonamide to the η2-alkene gold complex at the terminal position of the 1,3-diene resulted in the formation of the fused bicyclic ring with a newly formed Au-C bond at the allylic position. Allylic rearrangement of the η1-allylgold complex followed by protodemetalation provided the fused heterobicyclic skeletons and regenerated the catalyst.

AB - The gold(I)-catalyzed intramolecular hydroamination of cyclohexa-1,3-dienes bearing an arylsulfonamide at the C-5 position proceeds in a 1,4-addition manner to afford hexahydroindole derivatives in a diastereoselective fashion and in good yields, whereas octahydrocyclohepta[b]pyrrole derivatives can be obtained from seven-membered ring substrates under the same reaction conditions. Coordination of the gold(I) species to the 1,3-diene at the double bond adjacent to the arylsulfonamide tether gave an η2-alkene gold complex. The anti-attack of the sulfonamide to the η2-alkene gold complex at the terminal position of the 1,3-diene resulted in the formation of the fused bicyclic ring with a newly formed Au-C bond at the allylic position. Allylic rearrangement of the η1-allylgold complex followed by protodemetalation provided the fused heterobicyclic skeletons and regenerated the catalyst.

KW - Cycloheptadiene

KW - Cyclohexadiene

KW - Gold-catalyzed

KW - Hexahydroindoles

KW - Hydroamination

KW - Intramolecular

KW - Octahydrocyclohepta[b]pyrroles

KW - Sulfonamide

UR - http://www.scopus.com/inward/record.url?scp=65549099123&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=65549099123&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2009.04.064

DO - 10.1016/j.tet.2009.04.064

M3 - Article

AN - SCOPUS:65549099123

VL - 65

SP - 4789

EP - 4794

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 25

ER -