Application of chiral, cyclic sulfites

Various organometallic species in THF were investigated (Table 2.11) in Kagan s initial study [33], and the range was later extended [34]. 

Enantiomerically pure t-butyl alkyl sulfoxides were isolated from (35) (R =Bu ), as shown in Table 2.12. The displacement reactions were found to proceed with complete inversion of configuration at sulfur. 

The stereoselective 1,4-addition reactions of f-butyl alkyl sulfoxides have been investigated, but prior to Kagan s work [35] (and more recently the work of Khiar and colleagues) [36], their preparation in an enantiomerically pure form had 

The results for the preparation of dialkyl or alkyl aryl sulfoxides are shown in Table 2.13. 

A general trend clearly emerges. When R is bulky, the regioselective cleavage gives mainly (35) however, when R is small, sulhnate (34) is the major product. No formation of symmetrical, achiral sulfoxides was observed using Grignard 

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