Sulfoximines: Structures, Properties and Synthetic Applications

Abstract

This review presents a comprehensive treatment of sulfoximine chemistry particularly emphasising synthetic developments and structural work after 1985. Following a brief introduction, the structures and properties of sulfoximines and metallated sulfoximines are discussed. The second section deals with the preparation of sulfoximines emphasising new methods. The main part of the review is concerned with reactions of sulfoximines. The material in this section is organised based on the reactivity pattern displayed by the various sulfoximines. Therefore they are grouped roughly into three classes of compounds. The first group of sulfoximines comprises compounds acting as C-nucleophiles, the second one contains electrophilic sulfoximines and the last group is made up of sulfoximines being useful as (chiral) ligands particularly for transition metals. Finally the ability of sulfoximines to act as "chiral chemical chameleons" and their rôle in biological and medicinal chemistry is briefly discussed.

Modular Asymmetric Synthesis of Functionalized Azaspirocycles Based on the Sulfoximine Auxiliary

“…16 The synthetic approach to azaspirocycles described here is based on a two-step strategy in which the carbocycle with the tertiary C atom bearing the amino group is constructed (Scheme 4). This first part should take advantage of the methods developed in our group for the synthesis of β-and γ-amino acids from allylic sulfoximines.…”

“…They show a unique combination of features, including chirality, carbanion stabilization, nucleofugacity, basicity, nucleophilicity, and a low redox potential ( Figure 8). 16,20,21 …”

A Method for the Conversion of Sulfoximines to Sulfones: Application to Polymer-Bound Sulfoximines and to the Synthesis of Chiral Sulfones

“…Because of this combination, application of sulfoximines to solid-phase asymmetric synthesis would be highly interesting. [4,5] The ready alkylation, acylation, sulfonylation, and silylation of N-H sulfoximines at the N atom [1][2][3] should allow for the synthesis of various polymer-bound sulfoximines III from appropriately functionalized polymers I and enantiopure N-H sulfoximines II (Scheme 1). Deprotonation of sulfoximine III at the α-position and a subsequent functionalization would lead to the polymer-bound modified sulfoximine IV.…”

“…Deprotonation of sulfoximine III at the α-position and a subsequent functionalization would lead to the polymer-bound modified sulfoximine IV. Because of the nucleofugacity and the redox potential of the sulfonimidoyl group, [1][2][3] cleavage of IV to the sulfoximine-free chiral compounds V and VI by substitution and reduction, respectively, can be envisioned. [1][2][3] In addition to the substitution and reduction of sulfoximines, the development of a method for their quantitative conversion into the corresponding sulfones (VIII Ǟ IX) would be highly attractive.…”

“…[1][2][3] The sulfonimidoyl group not only frequently provides for a high asymmetric induction, but has also an almost unique array of synthetically attractive features of such as nucleofugacity, basicity, nucleophilicity, carbanion stabilization, and a favorable redox potential. Because of this combination, application of sulfoximines to solid-phase asymmetric synthesis would be highly interesting.…”