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Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OiPr)4

✍ Scribed by Jincheng Mao; Boshun Wan; Fan Wu; Shiwei Lu

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 94 KB
Volume: 17
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.20165

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✦ Synopsis

Abstract

Ephedrine‐derived sulfamide–amine alcohol 3 was found to be an effective catalyst for the asymmetric phenylacetylene addition to aldehydes at room temperature without using Ti(O^i^Pr)~4~ and Zn(OTf)~2~. It afforded the propargylic alcohols in high yields (up to 99%) and good enantioselectivities (up to 84% ee), which were much higher than that based on N‐methylephedrine under the same reaction conditions. Its weakly coordinative sulfonamide moiety of the ligand plays an important role for further acceleration and stereocontrol in the alkynylation. Chirality 17:245–249, 2005. © 2005 Wiley‐Liss, Inc.

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