期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 40, 页码 14027-14029出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja106674n
关键词
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资金
- National Science Foundation [CHE-0715491, CHE-9208463, CHE-9629688]
- NIH [R01 GM67163, RR08389-01]
- Abbott Laboratories
Rhodium complexes of diazaphospholane ligands catalyze the asymmetric hydroformylation of N-vinyl carboxamides, allyl ethers, and allyl carbamates; products include 1,2- and 1,3-aminoaldehydes and 1,3-alkoxyaldehydes. Using glass pressure bottles, short reaction times (generally less than 6 h), and low catalyst loading (commonly 0.5 mol %), 20 substrates are successfully converted to chiral aldehydes with useful regioselectivity and high enantioselectivity (up to 99% ee). Chiral Roche aldehyde is obtained with 97% ee from the hydroformylation of allyl silyl ethers. Commonly difficult substrates such as 1,1- and 1,2-disubstituted alkenes undergo effective hydroformylation with 89-97% ee and complete conversion for six examples. Palladium-catalyzed aerobic oxidative amination of allyl benzyl ether followed by enantioselective hydroformylation yields the beta(3)-aminoaldehyde with 74% ee.
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