{"title":"Syntheses of natural and non-natural β-amino acids using racemic and enantioselective sulfamate-tethered aza-Michael cyclization reactions","authors":"Mintu Munda, Harshit Joshi, Shyam Sathyamoorthi","doi":"10.1016/j.tet.2025.134845","DOIUrl":null,"url":null,"abstract":"<div><div>We detail the preparation of a library of ten β-amino acids (7 racemic and 3 scalemic), highlighting our laboratory's racemic and enantioselective sulfamate-tethered <em>aza</em>-Michael cyclization reactions. All ten syntheses proceed from oxathiazinane heterocycles furnished by reactions invented in our laboratory. This work raises the prominence of sulfamate-tethered <em>aza</em>-Michael technology and advocates for the more general use of sulfamates in olefin functionalization processes.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134845"},"PeriodicalIF":2.2000,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025004016","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We detail the preparation of a library of ten β-amino acids (7 racemic and 3 scalemic), highlighting our laboratory's racemic and enantioselective sulfamate-tethered aza-Michael cyclization reactions. All ten syntheses proceed from oxathiazinane heterocycles furnished by reactions invented in our laboratory. This work raises the prominence of sulfamate-tethered aza-Michael technology and advocates for the more general use of sulfamates in olefin functionalization processes.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.