Synthesis 2021; 53(15): 2570-2582
DOI: 10.1055/a-1426-4744
short review

Syntheses and Transformations of Sulfinamides

Qiaoling Zhang
,
Jufang Xi
,
He Ze
,
We are thankful to the National Natural Science Foundation of China (No. 20672088 and No. 21372034) and the State Key Laboratory of Geohazard Prevention and Geoenvironment Protection (No. SKLGP2020Z003) for their financial support.


Abstract

Sulfinamides, especially enantiopure sulfinamides, are widely used in organic and medicinal synthesis. Syntheses and transformations of racemic and enantioenriched sulfinamides have achieved great progress. Especially sulfinamides demonstrate interesting and valuable reactivity, which deserves to be pertinent. This review summarizes the latest development in the synthesis and transformation of sulfinamides and will be helpful for future related research.

1 Introduction

2 Synthesis of Sulfinamides

2.1 Synthesis of Racemic Sulfinamides

2.2 Synthesis of Enantiomerically Pure Sulfinamides

2.3 Synthesis of Other Sulfinamides

3 Transformations of Sulfinamides

3.1 Condensation with Aldehydes and Ketones

3.2 Reaction with Alkynes

3.3 Reaction with Alkenes

3.4 Reaction with Aryl and Alkyl Halides

3.5 Reaction with Alcohols, Dibenzyl Ether, and Benzyl Mercaptan

3.6 Synthesis of tert-Butyldisulfanyl-Substituted Hetarenes

3.7 Synthesis of Asymmetric Sulfides

3.8 Synthesis of N-Phosphino-sulfinamide Ligands

3.9 Asymmetric Synthesis of γ-Amino Acids

3.10 Sulfonylation of Heterocyclic Compounds

4 Summary and Outlook



Publication History

Received: 16 January 2021

Accepted after revision: 11 March 2021

Publication Date:
11 March 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
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