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1,5-Benzodithiepan-3-one 1,5-dioxide: A novel chiral auxiliary for asymmetric desymmetrization of meso-1,2-diols

✍ Scribed by Naoyoshi Maezaki; Atsunobu Sakamoto; Motohiro Soejima; Ikuyo Sakamoto; Li Ying Xia; Tetsuaki Tanaka; Hirofumi Ohishi; Ken-ichi Sakaguchi; Chuzo Iwata

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 208 KB
Volume: 7
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(96)00362-x

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✦ Synopsis

A novel C~-symmetric bis-sulfoxide 1 was synthesized as a chiral auxiliary for asymmetric desymmetrization of meso-1,2-diols. cis-Cyclohexane-1,2-dioi and cis-cyclopentane-1,2-diol were desymmetrized via acetalization with I followed by basepromoted acetal cleavage with high diastereoselectivity (>96% d.e.).

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