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

被引：77

作者：

Matlock, Johnathan V. ^{[1
]}

Svejstrup, Thomas D. ^{[1
]}

Songara, Pradip ^{[1
]}

Overington, Sarah ^{[1
]}

McGarrigle, Eoghan M. ^{[2
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] Univ Coll Dublin, Sch Chem, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 20期

基金：

英国工程与自然科学研究理事会; 爱尔兰科学基金会;

关键词：

VINYL SULFONIUM SALTS; ONE-STEP SYNTHESIS; SNAP REAGENTS; SUBSTITUTED MORPHOLINES; VINYLSULFONIUM SALTS; ASYMMETRIC-SYNTHESIS; TANDEM REACTIONS; AMINO-ALCOHOLS; THIOMORPHOLINES; PIPERAZINES;

D O I：

10.1021/acs.orglett.5b02516

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 alpha-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.

引用

页码：5044 / 5047

页数：4

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