Asymmetric addition of phenylacetylene to aromatic ketones catalyzed by zinc or titanium complexes with chiral hydroxysulfonamide

Various new chiral hydroxysulfonamide ligands (3a–3n, 4a–4d) were prepared. Compounds 3a, 3g, 3i, 3k–3n, 4a–4d could accelerate the reaction and reduce reaction time, and 3a, 3g, 3i, 3k–3n catalyzed the reaction without titanium. The results obtained were promising in terms of yields and enantiomeri...

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Published in:Chirality (New York, N.Y.) N.Y.), 2009-04, Vol.21 (4), p.473-479
Main Authors: Zhou, Yi-Feng, Han, Zhi-Jian, Qiu, Li, Liang, Jin-Yan, Ren, Feng-Bo, Wang, Rui
Format: Article
Language:English
Subjects:
Acetophenones - chemistry
Acetylene - analogs & derivatives
Acetylene - pharmacology
Alcohols - chemistry
asymmetric catalysis
Catalysis
Chemistry, Organic - methods
chiral hydroxysulfonamide
ketones
Ketones - metabolism
Ligands
Models, Chemical
phenylacetylene
Stereoisomerism
Sulfonamides - chemistry
Temperature
Time Factors
Titanium - chemistry
Zinc - chemistry
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Summary:Various new chiral hydroxysulfonamide ligands (3a–3n, 4a–4d) were prepared. Compounds 3a, 3g, 3i, 3k–3n, 4a–4d could accelerate the reaction and reduce reaction time, and 3a, 3g, 3i, 3k–3n catalyzed the reaction without titanium. The results obtained were promising in terms of yields and enantiomeric excesses (3k up to 85% ee, 4a up to 83% ee). Chirality, 2009. © 2008 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.20622