Scientific article
English

Intramolecular Asymmetric Amidations of Sulfonamides and Sulfamates Catalyzed by Chiral Dirhodium(II) Complexes

Published inHelvetica Chimica Acta, vol. 87, no. 7, p. 1607-1615
Publication date2004
Abstract

Enantioselective intramolecular amidation of aliphatic sulfonamides was achieved for the first time by means of chiral carboxylatodirhodium(II) catalysts in conjunction with PhI(OAc)₂ and MgO in high yields and with enantioselectivities of up to 66% (Scheme 3, Table 1). The best results were obtained with [Rh₂{(S)‐nttl)₄] and [Rh₂{(R)‐ntv)₄] as catalysts ((S)‐nttl=(αS)‐α‐(tert‐butyl)‐1,3‐dioxo‐2H‐benz[de]isoquinoline‐2‐acetato, (R)‐nto=(αR)‐α‐isopropyl‐1,3‐dioxo‐2H‐benz[de] isoquinoline‐2‐acetato). In addition, these carboxylatodirhodium(II) catalysts were also efficient in intramolecular amidations of aliphatic sulfamates esters, although the enantioselectivity of these latter reactions was significantly lower (Scheme 4, Table 3).

Citation (ISO format)
FRUIT, Corinne, MULLER, Paul. Intramolecular Asymmetric Amidations of Sulfonamides and Sulfamates Catalyzed by Chiral Dirhodium(II) Complexes. In: Helvetica Chimica Acta, 2004, vol. 87, n° 7, p. 1607–1615. doi: 10.1002/hlca.200490148
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
Additional URL for this publicationhttp://doi.wiley.com/10.1002/hlca.200490148
Journal ISSN0018-019X
313views
0downloads

Technical informations

Creation28/05/2019 16:57:00
First validation28/05/2019 16:57:00
Update time15/03/2023 18:11:22
Status update15/03/2023 18:11:22
Last indexation31/10/2024 14:34:13
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack