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Highly enantioselective alkynylation of aldehydes using a new BINOL/Ti(OiPr)4/chiral sulfonamide catalyst system

✍ Scribed by Xingshu Li; Gui Lu; Xian Jia; Yinuo Wu; Albert S. C. Chan

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 104 KB
Volume: 19
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.20433

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✦ Synopsis

Abstract

A series of sulfonamides (2–4) were prepared from natural amino acids and used as additives in the BINOL‐Ti(O__i__Pr)~4~ catalyzed enantioselective alkynylation of aldehydes. The reactions proceeded smoothly with good yields and very high ee's (up to 99%) in most cases. Chirality 19:638–641, 2007 © 2007 Wiley‐Liss, Inc.

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## Abstract A new catalytic system, generated from the readily available and inexpensive β‐sulfonamide alcohol L\*, Ti(O^i^Pr)~4~, Et~2~Zn, and tertiary amine base (R~3~N), effectively catalyzes the enantioselective addition of various terminal alkynes including some quite challenging alkynes to al