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Catalytic enantioselective cyclopropanation of allylic alcohols using recyclable fluorous disulfonamide ligand

✍ Scribed by Tsuyoshi Miura; Keisuke Itoh; Yumi Yasaku; Naka Koyata; Yasuoki Murakami; Nobuyuki Imai

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 162 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.07.125

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✦ Synopsis

Cyclopropanation of allylic alcohols with Et 2 Zn and CH 2 I 2 in the presence of a catalytic amount of fluorous disulfonamide 3 afforded the corresponding cyclopropylmethanols in 69-96% yield with 49-83% ee. The fluorous ligand 3 was readily recovered from the reaction mixture by the fluorous solid-phase extraction (FSPE) and could be reused without a significant loss of the catalytic activity and enantioselectivity.

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