Highly enantioselective addition of terminal alkynes to aldehydes catalyzed by a new chiral β-sulfonamide alcohol/Ti(OiPr)4/Et2Zn/R3N catalyst system

A new catalytic system, generated from the readily available and inexpensive β‐sulfonamide alcohol L*, Ti(OiPr)4, Et2Zn, and tertiary amine base (R3N), effectively catalyzes the enantioselective addition of various terminal alkynes including some quite challenging alkynes to aldehydes in good yields...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2009-02, Vol.21 (2), p.316-323
Main Authors: Qiu, Li, Wang, Quan, Lin, Li, Liu, Xiaodong, Jiang, Xianxing, Zhao, Qingyang, Hu, Guowen, Wang, Rui
Format: Article
Language:English
Subjects:
aldehydes
Aldehydes - chemistry
Alkynes - chemistry
Amines - chemistry
Catalysis
enantioselective addition
Organometallic Compounds - chemistry
Pentanols - chemistry
Stereoisomerism
Substrate Specificity
sulfonamide alcohol
Sulfonamides - chemistry
terminal alkynes
tertiary amine base
Tosyl Compounds - chemistry
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Summary:A new catalytic system, generated from the readily available and inexpensive β‐sulfonamide alcohol L*, Ti(OiPr)4, Et2Zn, and tertiary amine base (R3N), effectively catalyzes the enantioselective addition of various terminal alkynes including some quite challenging alkynes to aldehydes in good yields and excellent enantioselectivities. Up to 96% yield and >99% enantioselectivity were achieved with the use of N,N‐diisoproylethylamine (DIPEA) as an additive in this asymmetric addition. Chirality, 2009. © 2008 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.20583