New Routes to N-Alkylated Cyclic Sulfamidates

BOC- and dibenzosuberyl-protected chiral and hindered cyclic sulfamidates ([1,2,3]-oxathiazolidine-2,2-dioxides) were synthesized and subsequently deprotected using trifluoroacetic acid. The resulting crystalline sulfamidates were then used in several alkylation reactions involving benzyl bromide an...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 67; no. 15; pp. 5164 - 5169
Main Authors Posakony, Jeffrey J, Grierson, John R, Tewson, Timothy J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.07.2002
Amer Chemical Soc
Subjects
Alkylation
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques - methods
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
ALCOHOLS
ALPHA-AMINO-ACIDS
LIMITATIONS
SCOPE
DERIVATIVES
Sulfanilamide derivatives
Aminoalcohol
Oxygen sulfur nitrogen heterocycle
Deprotection
Mitsunobu reaction
Chemical synthesis
Alkylation
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Summary:BOC- and dibenzosuberyl-protected chiral and hindered cyclic sulfamidates ([1,2,3]-oxathiazolidine-2,2-dioxides) were synthesized and subsequently deprotected using trifluoroacetic acid. The resulting crystalline sulfamidates were then used in several alkylation reactions involving benzyl bromide and alcohols in a versatile route to cyclic sulfamidates with differing N-alkyl substituents.
Bibliography:ark:/67375/TPS-83586V07-X
istex:3E71141CC2EB55547445CC5D0E0B4E1423F4D704
Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0157019