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Enantioselective Addition of Phenylacetylene to Ketones Catalyzed by Titanium(IV) Complexes of N-Sulfonylated β-Amino Alcohols

✍ Scribed by Shao-Hua Wang; Yong-Qiang Tu; Peng Chen

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
53 KB
Volume
24
Category
Article
ISSN
0256-7660

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✦ Synopsis

Abstract

The easily prepared and recoverable chiral N‐sulfonylated β‐amino alcohol 2 in combination with Ti(OPr‐i)~4~was found to be an effective chiral catalyst for the enantioselective addition of alkynylzinc to ketones, which gave the useful products, i.e. chiral tertiary propargyl alcohols, with the ee up to 92%.

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The enantioselective formation of C À C bonds is an area of intense research. [1,2] The asymmetric addition of alkynyl reagents to aldehydes is very useful for the synthesis of chiral secondary propargyl alcohols, which are important building blocks for many chiral organic compounds. [3] Several stu