Abstract
The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from tert-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the tert-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral N-tert-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format.
Highlights
Chiral imines derived from tert-butanesulfinamide have been extensively used as electrophiles in a wide range of reactions
The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the tert-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles
The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral N-tert-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products
Summary
Saturated nitrogen-containing three-membered heterocycles have attracted increasing interest in recent years because compounds with this structural motif display quite diverse pharmacological activities. The group of Njardarson found that the reaction of different aromatic and aliphatic chiral imines (SS)-14 with the dienolate resulting from the deprotonation of bromomethyl butenolide 29 in THF at Scheme 9: Synthesis of vinylaziridines 27 from aldimines 14 and α-bromoesters 26, and proposed transition state leading to the major diastereoisomer. The addition of lithium metaloenamine took place through and open transition state to the Re face of the imine (RS)-14, followed by an intramolecular nucleophilic substitution to form the aziridines ring. The nucleophilic addition of metaloenaime occurred through a cyclic transition state to the Si face of the imine (RS)-14 In this way, both cis-aziridines diastereoisomers 36 and 32 were formed from the same chiral imine 14 and arylnitriles 34 (Scheme 12). They observed an intramolecularly intermediate Cu(III) species, and the sulfinamide acts as a direction group and nucleophile [75] (Scheme 14)
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