Synthesis of 6- and 7-Membered N-Heterocycles Using α-Phenylvinylsulfonium Salts

Johnathan V. Matlock, Thomas D. Svejstrup, Pradip Songara, Sarah Overington, Eoghan M McGarrigle*, Varinder K Aggarwal

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

51 Citations (Scopus)
290 Downloads (Pure)

Abstract

A concise synthesis of stereodefined C-substituted morpholines, piperazines, azepines, and oxazepines in moderate to excellent yields (27% to 75%) is reported by reaction of 1,2- or 1,3-amino alcohol/1,2- or 1,3-diamine with an α-phenylvinylsulfonium salt. High levels of regio- and diastereoselectivity (from 2:1 to >20:1) are observed through judicious choice of base (Cs2CO3) and solvent (CH2Cl2). Reactions are performed at ambient temperature and open to air and do not require anhydrous solvent. The deprotection of the N-sulfonamide protecting groups (N-Ts and N-Ns) is also demonstrated. Factors affecting regio- and diastereocontrol are discussed.

Original languageEnglish
Pages (from-to)5044-5047
Number of pages4
JournalOrganic Letters
Volume17
Issue number20
Early online date30 Sep 2015
DOIs
Publication statusPublished - 16 Oct 2015

Structured keywords

  • BCS and TECS CDTs

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