Chiral Hetero- and Carbocyclic Compounds from the Asymmetric Hydrogenation of Cyclic Alkenes

被引:43
|
作者
Verendel, J. Johan [1 ]
Li, Jia-Qi [1 ]
Quan, Xu [1 ]
Peters, Byron [1 ]
Zhou, Taigang [1 ]
Gautun, Odd R. [2 ]
Govender, Thavendran [3 ]
Andersson, Pher G. [1 ,3 ]
机构
[1] Uppsala Univ, Dept Biochem & Organ Chem, S-75123 Uppsala, Sweden
[2] Norwegian Univ Sci & Technol NTNU, Dept Chem, NO-7491 Trondheim, Norway
[3] Univ KwaZulu Natal, Sch Chem, Durban, South Africa
基金
瑞典研究理事会;
关键词
asymmetric synthesis; heterocyclic compounds; homogeneous catalysis; hydrogenation; iridium; MODIFIED PALLADIUM CATALYST; ENANTIOSELECTIVE HYDROGENATION; IRIDIUM CATALYSTS; CONJUGATE REDUCTION; OXAZOLINE LIGANDS; OLEFINS; COMPLEXES; IMINES; ROUTE; ACID;
D O I
10.1002/chem.201104073
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several types of chiral hetero- and carbocyclic compounds have been synthesized by using the asymmetric hydrogenation of cyclic alkenes. N,P-Ligated iridium catalysts reduced six-membered cyclic alkenes with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five-membered cyclic alkenes was generally less selective, giving modest enantiomeric excesses. The stereoselectivity of the hydrogenation depended more strongly on the substrate structure for the five- rather than the six-membered cyclic alkenes. The major enantiomer formed in the reduction of six-membered alkenes could be predicted from a selectivity model and isomeric alkenes had complementary enantioselectivity, giving opposite optical isomers upon hydrogenation. The utility of the reaction was demonstrated by using it as a key step in the preparation of chiral 1,3-cis-cyclohexane carboxylates.
引用
收藏
页码:6507 / 6513
页数:7
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