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2005
Sulfonic acids and esters
Q 0550
Efficient Asymmetric Synthesis of α-Alkylated Benzylic Methyl Sulfonates. —
benzylic sulfonic esters bearing an allofuranose moiety as alcohol auxiliary
32- 102 Lithiated
react with alkyl halides to give alkylated products in excellent diastereomeric excesses.
Racemization-free cleavage conditions provide the highly enantiopure sulfonic acid derivatives. The present method seems to be limited to benzylic types of sulfonates since
allylic and alkyl lithiosulfonates give the products with only 75% or no diastereoselectivity, respectively. — (ENDERS*, D.; VIGNOLA, N.; BERNER, O. M.;
HARNYING, W.; Tetrahedron 61 (2005) 13, 3231-3243; Inst. Org. Chem., RWTH
Aachen, D-52074 Aachen, Germany; Eng.) — Klein
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