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Highly enantioselective addition of terminal alkynes to aldehydes catalyzed by a new chiral β‐sulfonamide alcohol/Ti(O i Pr) 4 /Et 2 Zn/R 3 N catalyst system
Author(s) -
Qiu Li,
Wang Quan,
Lin Li,
Liu Xiaodong,
Jiang Xianxing,
Zhao Qingyang,
Hu Guowen,
Wang Rui
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20583
Subject(s) - enantioselective synthesis , chemistry , sulfonamide , catalysis , chirality (physics) , alcohol , amine gas treating , yield (engineering) , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry , chiral symmetry breaking , physics , materials science , quantum mechanics , nambu–jona lasinio model , quark , metallurgy
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 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.