Synthesis of chiral norbornane derivatives as γ-amino alcohol catalysts: the effect of the functional group positions on the chirality transfer |
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| Institution: | 1. Department of Chemistry, Southern Methodist University, Box 0314, Dallas, TX 75275-0314, United States;2. Hockaday School, 11600 Welch Rd, Dallas, TX 75229, United States;3. University of Texas at Austin, Austin, TX 78712, United States;4. Plano West Senior High School, 5601 W. Parker Rd, Plano, TX 75093, United States;5. Department of Pharmaceutic Sciences, College of Pharmacy, Western University of Health Sciences, Pomona, CA 91766, United States;6. Center for Drug Discovery, Design, and Delivery, Dedman College, Southern Methodist University, Dallas, TX 75275, United States;1. C.N.R. Istituto di Farmacologia Traslazionale, UOS Cagliari, Edificio 5, Loc. Piscinamanna, 09010 Pula, CA, Italy;2. Neuroscienze PharmaNess S.c.a r.l., Edificio 5, Loc. Piscinamanna, 09010 Pula, CA, Italy;3. Dipartimento di Chimica e Farmacia, Università di Sassari, Via F. Muroni 23/A, 07100 Sassari, Italy;1. Namik Kemal University, Muratli Vocational School, Department of Chemical Technology, Muratli, Tekirdag, Turkey;2. Namik Kemal University, Faculty of Science and Arts, Department of Chemistry, 59030 Tekirdag, Turkey;3. Uludag University, Faculty of Science and Arts, Department of Chemistry, 16100 Bursa, Turkey;1. Faculty of Chemistry, University of Belgrade, Studentski trg 16, POB 51, 11158 Belgrade 118, Serbia;2. Innovation Centre, Faculty of Chemistry, 11000 Belgrade, Serbia;1. Faculty of Agriculture and Life Science, Hirosaki University, 3-Bunkyo-cho, Hirosaki, 036-8561, Japan;2. The United Graduate School of Agricultural Sciences, Iwate University, Morioka, 020-8550, Japan;3. Graduate School of Integrated Arts and Sciences, Hiroshima University, 1-7-1, Kagamiyama, Higashi-Hiroshima, 739-8521, Japan;4. Graduated School of Science and Technology, Hirosaki University, 3-Bunkyo-cho, Hirosaki, 036-8561, Japan;1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Acad. Kuprevicha Str. 5/2, 220141 Minsk, Belarus;2. Institute for Single Crystals, National Academy of Sciences of Ukraine, pr. Lenina 60, Kharkiv 61001, Ukraine;3. Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga LV-1048, Latvia |
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| Abstract: | Starting from (1S,4R) chiral ketone (+)-6, we developed a synthetic route to the synthesis of new chiral γ-amino alcohols (+)- and (−)-syn-2-amino-7-hydroxy norbornane derivatives with excellent yields and enantiomeric excesses (up to 99%). These compounds were tested as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde presenting moderate results. The results obtained, compared with others previously reported, showed that the relative disposition of the amino and hydroxyl groups on C(2) and C(7) positions, play an important role in the catalytic activity. |
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