Journal of Organometallic Chemistry p. 23 - 32 (2008)
Update date:2022-07-30
Topics:
La?, Richard
Chanon, Florence
Roussel, Christian
Sanz, Martial
Vanthuyne, Nicolas
Daran, Jean-Claude
Asymmetric cyclopentadienes and indenes are easily prepared by nucleophilic attack of LiCp or LiInd on tosylate or triflate of ethyl (S)-(-) lactate. The selectivity of the reaction depends on the nature of the leaving group. This is particularly true in the case of the reaction of LiCp with sulfonates of ethyl (S)-(-) lactate. Indeed, only the monosubstituted cyclopentadiene lactate 2 is obtained from the triflate 6, whereas from the tosylate 1, besides 2 (20%) a 1,3-disubstituted cyclopentadiene lactate 3 is isolated (16.5%). From cyclopentadiene and indene lactate 2 and 7, optically active β-hydroxycyclopentadiene 10 and β-hydroxyindene 11 are obtained by reduction with LiAlH4. Two rhodium(I) complexes 14 and 15 have been synthesized from (R,S)-2-(cyclopentadienyl)N,N-dimethylpropanamide 12 and (S)-2-(cyclopentadiene)propan-1-ol 10, respectively. The molecular structure of these complexes has been determined. Analytical and preparative chiral HPLC have been used to determine the optical purity of the ligands and to isolate enantiopure cyclopentadienyl complexes from racemic or enantiomerically enriched rhodium(I) complexes.
View MoreTianjin Jingye Fine Chemicals Co., Ltd.
Contact:+86-15722078107; +86-22-26911407
Address:Bohua Fine Chemicals Base of Petrochemical Industry Park, Nanhuan Road, Dagang District, Tianjin, 300271, P. R. China
Chongqing Yawei Fine Chemical Co.,Ltd
Contact:0086-23-62849407
Address:Ziyou village, Nanquan town, Banan district, Chongqing China
website:http://www.truewingroup.com
Contact:86-311-66699812
Address:NO.600 ZHONGSHAN EAST ROAD SHIJIAZHUANG
website:http://www.simagchem.com
Contact:+86-592-2680277
Address:21/F Hualong Office Building,No.6 Hubin East Road, Xiamen,China
Ningbo Tide Imp. & Exp. Co., Ltd.
Contact:+86-571-8993 7933; +86-571-8993 6453
Address:7/F Anno Domini Building, Tower South, 8 Qiu Shi Road,Hangzhou,China.
Doi:10.1021/jo050574s
(2005)Doi:10.1021/jo7021229
(2008)Doi:10.1016/S0040-4039(00)98242-X
(1985)Doi:10.1002/ejic.200400847
(2005)Doi:10.1021/ol049159x
(2004)Doi:10.1248/cpb.44.1181
(1996)