Novel asymmetric desymmetrization of meso-1,2-diols via diastereoselective β-elimination of chiral α-arylsulfinyl acetals

Enantioselective desymmetrization of meso-1,2-diols was accomplished via diastereoselective CO bond fission of acetals derived from various optically active β-ketosulfoxides with high diastereoselectivities. The substituent at the γ-position of the β-ketosulfoxide plays an important role in this cl...

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Bibliographic Details
Published in:Tetrahedron 1996-05, Vol.52 (19), p.6527-6546
Main Authors: Naoyoshi, Maezaki, Motohiro, Soejima, Miwako, Takeda, Atsunobu, Sakamoto, Yûki, Matsumori, Tetsuaki, Tanaka, Chuzo, Iwata
Format: Article
Language:English
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Summary:Enantioselective desymmetrization of meso-1,2-diols was accomplished via diastereoselective CO bond fission of acetals derived from various optically active β-ketosulfoxides with high diastereoselectivities. The substituent at the γ-position of the β-ketosulfoxide plays an important role in this cleavage. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00294-3