Chemical Communications p. 2497 - 2504 (1996)
Update date:2022-08-05
Topics:
Iwata, Chuzo
Takemoto, Yoshiji
The ability of iron tricarbonyl units to control the regio- and stereo-chemistry of nucleophilic addition to a neighbouring C=X (X = O, N) double bond and 1,5-nucleophilic substitution via a η5-cation intermediate are described. We investigated the potential of acyclic [Fe(diene)(CO)3] complexes as chiral auxiliaries for the asymmetric synthesis of natural products. The asymmetric syntheses of (+) and (-)-frontalin, a hydroxyethylidene dipeptide isostere, a piperidine alkaloid (SS20846A), and N-Boc-O-Me-(2R,3S,5E,7E)-2-aminotetradeca-5,7-dien-3-ol were achieved by using the stereodirecting ability and mobility of the Fe(diene)(CO)3 group. In addition, we developed an efficient method for synthesizing chiral dienal Fe(CO)3 complexes, which are versatile starting materials for the asymmetric synthesis of the biologically active natural products described above.
Contact:+86-532-80762375
Address:No. 6, Hongkong Middle Road, Qingdao, China
Contact:+86-531-58668191 58668193 58668196 58661173
Address:No 55,Beixiaoxinzhuang West Street,Jinan City, Shandong Province
Tianjin Tensing Fine Chemical Research Develop Centre
Contact:86-022-23718576,13032267585
Address:2-2-201,13 Guiyuan road,Huayuan Industry district,Tianjin,china
Hubei Danao Pharmaceutical Co.,Ltd.
website:http://www.danaopharm.com
Contact:+86-719-5251167
Address:Fandan Road,Danjiangkou,Hubei
Jinan Hongfangde Pharmatech Co.,Ltd
Contact:86-531-88870908
Address:F Bldg. West Unit North Area of Univ. Tech. Garden Xinyu Rd. Jinan New & High Tech Industry Development Zone Shandong, China
Doi:10.1016/S0040-4039(01)01688-4
(2001)Doi:10.1021/acs.joc.8b02002
(2018)Doi:10.1016/j.tetasy.2012.07.013
(2012)Doi:10.1039/c2ob07031f
(2012)Doi:10.1016/j.mencom.2018.07.035
(2018)Doi:10.1021/ol017093p
(2002)
