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39.4.2.1.2.2.2 Variation 2: Using Alkyl Peroxides and Chiral Metal Catalysts

DOI: 10.1055/sos-SD-039-00359

García Ruano, J. L.; Cid, M. B.; Martín-Castro, A. M.; Alemán, J.Science of Synthesis, (200839322.

The successes obtained with the Sharpless reagent, titanium(IV) isopropoxide(R,R)-diethyl tartrate, for asymmetric epoxidations prompted other authors to explore different oxidizing reactions with the same catalyst. Almost simultaneously, Kagan[‌496‌] and Modena[‌497‌] reported in 1984 that modified Sharpless reagents are efficient in the asymmetric oxidation of sulfides. Since then, some other modifications have appeared in the literature involving changes in the diol forming the complexes with the metal. They are presented here according to the nature of the alcohol acting as the metal ligand.

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M8 Meee (e) eee (%) (Meeeee) Meeee (%) Mee
(MM8)8Me 88 88 (e.e.) 88 [‌888‌]
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Meeee M8 Meeeeeeeee Meeeeeeeeeee ee (%) (Meeeee) Meeee (%) Mee
8 (MM8)8Me 88°M MMMe eeeeeee ee e-MeMMM 88 88 [‌888‌]
8 Me 88°M MMMe eeeeeee ee e-MeMMM 88.8 88 [‌888‌]
8 (MM8)8Me 88°M, 8e MMMe eeeeeee ee e-MeMMM 88 (M) 88 [‌888‌]
8 Me 88°M eMeMM eeeeeee ee M8M 88.8 (M) 88 [‌888‌]
8 (MM8)8Me 88°M eMeMM eeeeeee ee M8M 88.8 (M) 88 [‌888‌]
8 (MM8)8Me 88°M, 88e Me-MMMMe 88.8 (M) 88 [‌888‌]
8 Me 88°M, 88e Me-MMMMe 88.8 (M) 88 [‌888‌]
8 MM8MM8Me 88°M, 88e Me-MMMMe e 88 [‌888‌]
8 Me 88°M eeeeeeee eeeeeeee ee M8M 88.8 (M) 88 [‌888‌]

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Meeeee 888 Meeeeeeee ee Meee Meeeeee Meeeeeee ee Meeeeeeeee eeee 8,8-Me-8-eeeeeeee Meeeeee[‌888‌]

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Meeeee 888 Meeeeeeee ee Meeeeee Meeeeeee ee Meeeeeeeee ee eee Meeeeeeee ee (+)-Meeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeee Meeeee Meeeeeeeee 88; Meeeeee Meeeeeeee:[‌888‌]

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References


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