Synthesis of new, highly hindered C2-symmetric trans (2S,5S)-disubstituted pyrrolidines

被引:14
作者
Aggarwal, VK [1 ]
Sandrinelli, F [1 ]
Charmant, JPH [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0957-4166(02)00032-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:87 / 93
页数:7
相关论文
共 59 条
[31]   Chiral amino siloxy dienes in the Diels-Alder reaction:: Applications to the asymmetric synthesis of 4-substituted and 4,5-disubstituted cyclohexenones and the total synthesis of (-)-α-elemene [J].
Kozmin, SA ;
Rawal, VH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9562-9573
[32]  
KURSANOV DN, 1974, SYNTHESIS-STUTTGART, P633
[33]   A SHORT SYNTHESIS OF C-2 SYMMETRICAL (2S, 5S) PYRROLIDINE-2,5 DICARBOXYLIC-ACID, A CONSTITUENT OF RED ALGA SCHIZYMENIA-DUBYI [J].
LANGLOIS, N ;
ROJAS, A .
TETRAHEDRON, 1993, 49 (01) :77-82
[34]   SYNTHESIS OF ENANTIOMERICALLY PURE (2R,5R) DISUBSTITUTED PYRROLIDINES FROM D-MANNITOL [J].
MARZI, M ;
MINETTI, P ;
MISITI, D .
TETRAHEDRON, 1992, 48 (46) :10127-10132
[35]   SHORT-STEP SYNTHESIS OF CHIRAL C2-SYMMETRICAL 2,3,4,5-TETRASUBSTITUTED PYRROLIDINES FROM D-MANNITOL AND THEIR USE AS CHIRAL LIGANDS IN THE REACTION OF DIETHYLZINC AND BENZALDEHYDE [J].
MASAKI, Y ;
ODA, H ;
KAZUTA, K ;
USUI, A ;
ITOH, A ;
XU, F .
TETRAHEDRON LETTERS, 1992, 33 (35) :5089-5092
[36]   DIRECT CHAIN ELONGATION OF N-CARBAMOYLPYROGLUTAMATE - AN EFFICIENT SYNTHESIS OF (-)-PYRROLIDINE-2,5-DICARBOXYLIC ACID [J].
OHTA, T ;
HOSOI, A ;
KIMURA, T ;
NOZOE, S .
CHEMISTRY LETTERS, 1987, (10) :2091-2094
[37]   SELECTIVE REDUCTION OF DIARYL OR ARYL ALKYL ALCOHOLS IN THE PRESENCE OF PRIMARY HYDROXYL OR ESTER GROUPS BY ETHERATED BORON TRIFLUORIDE-TRIETHYLSILANE SYSTEM [J].
ORFANOPOULOS, M ;
SMONOU, I .
SYNTHETIC COMMUNICATIONS, 1988, 18 (08) :833-839
[38]   CHIRAL AUXILIARY-DIRECTED ASYMMETRIC NUCLEOPHILE ADDITIONS TO ARENE MANGANESE TRICARBONYL COMPLEXES [J].
PEARSON, AJ ;
ZHU, PY ;
YOUNGS, WJ ;
BRADSHAW, JD ;
MCCONVILLE, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10376-10377
[39]   Synthesis of 2,5-disubstituted pyrrolidines [J].
Pichon, M ;
Figadere, B .
TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :927-964
[40]   RADICAL-ADDITION TO AMIDE-SUBSTITUTED ALKENES - STEREOSELECTIVE INTERMOLECULAR RADICAL ADDITIONS [J].
PORTER, NA ;
SCOTT, DM ;
LACHER, B ;
GIESE, B ;
ZEITZ, HG ;
LINDNER, HJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8311-8312