(+)-Camphor-derived amino alcohols as ligands for the catalytic enantioselective addition of diethylzinc to benzaldehydes |
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| Institution: | 2. Key Laboratory of Modern Preparation of TCM, Jiangxi University of Traditional Chinese Medicine, Ministry of Education, Nanchang, Jiangxi Province, China;3. The North Carolina Arboretum Germplasm Repository, UNC Affiliate Campus, Asheville, NC, USA;4. College of Food Science and Engineering, Central South University of Forestry and Technology, Changsha, Hunan Province, China;5. Strategic Sourcing, Inc., Banner Elk, NC 28604, USA |
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| Abstract: | 1,7,7-Trimethyl-3-(pyrid-2-ylmethyl)bicyclo2.2.1]heptan-2-ol 4 and its 2-phenyl, 2-methyl and 2-butyl analogs 5–7 were synthesized, characterized and used as ligands for the addition of diethylzinc to benzaldehydes. Best results were attained with 5 mol% of amino alcohol trans-4 (2-exo,3-endo), in hexane/toluene at rt. Thus, (1S)-1-phenylpropanol was obtained in 96% yield and 89% e.e. An increase of the size of the 2-substituent had a dramatic effect on enantioselectivity and yield. |
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