Journal article
ASYMMETRIC SYNTHESIS OF SULTAMS AND SULFONAMIDES VIA DIASTEREOSELECTIVE REDUCTION OF N-SULFONYLIMINES
Phosphorus, sulfur, and silicon and the related elements, v 115(1), pp 85-91
01 Aug 1996
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
The diastereoselective reduction of both cyclic and acyclic camphor sulfonylimines was investigated. With cyclic camphor sulfonylimines 1, reduction using NaBH
4
in methanol afforded the corresponding camphorsultams 2 in 92-95% yield as single diastereomers with the exception of 1c where debromination occurred prior to reduction. For the large scale preparation of camphorsultam 1a and its derivatives, important chiral auxiliaries in asymmetric synthesis, reduction with NaBH
4
is the reagent of choice. Reduction of acyclic camphor sulfonylimines 7 to camphorsulfonamides 8 with the bulky reducing reagent, LiAI(OBu-i)
3
H afforded the highest de's (>90% de) and yields 90-95%.
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Details
- Title
- ASYMMETRIC SYNTHESIS OF SULTAMS AND SULFONAMIDES VIA DIASTEREOSELECTIVE REDUCTION OF N-SULFONYLIMINES
- Creators
- Franklin A. Davis - Temple UniversityPing Zhou - Drexel UniversityBang-Chi Chen - Drexel University
- Publication Details
- Phosphorus, sulfur, and silicon and the related elements, v 115(1), pp 85-91
- Publisher
- Taylor & Francis Group
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- [Retired Faculty]
- Web of Science ID
- WOS:A1996VK91100007
- Scopus ID
- 2-s2.0-0030495691
- Other Identifier
- 991019168056404721
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- Collaboration types
- Domestic collaboration
- Web of Science research areas
- Chemistry, Inorganic & Nuclear
- Chemistry, Organic