Highly enantioselective synthesis of 3-hydroxy-2-phenylpiperidine via the sharpless AD-reaction

被引:21
作者
Stadler, H [1 ]
Bös, M [1 ]
机构
[1] F Hoffmann La Roche & Co Ltd, Preclin Res, Div Pharma, CH-4070 Basel, Switzerland
关键词
D O I
10.3987/COM-99-8489
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric dihydroxylation (AD) of the silyl enol ether (3) provided after hydrolysis the hydroxy ketone (4). Subsequent hydrogenation yielded the title compound (1) as a diastereomeric mixture. The cis-isomer is an important building block for the synthesis of potent NK1 receptor antagonists.
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页码:1067 / 1071
页数:5
相关论文
共 11 条
[1]   Stereoselective synthesis of 2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenyl-1,4-oxazine [J].
Ashwood, MS ;
Cottrell, IF ;
Davies, AJ .
TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :957-963
[2]  
Baker R, European Patent, Patent No. [EP0528495A1, 0528495]
[3]  
CZAEAU P, 1989, J ORGANOMET CHEM, V201, pC9
[4]   2(S)-((3,5-bis(trifluoromethyl)benzyl)oxy)-3(S)-phenyl-4-((3-oxo-1,2,4-triazol-5-yl)methyl)morpholine .1. A potent, orally active, morpholine-based human neurokinin-1 receptor antagonist [J].
Hale, JJ ;
Mills, SG ;
MacCoss, M ;
Shah, SK ;
Qi, HB ;
Mathre, DJ ;
Cascieri, MA ;
Sadowski, S ;
Strader, CD ;
MacIntyre, DE ;
Metzger, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (09) :1760-1762
[5]   PIPERIDINE-ETHER BASED HNK(1) ANTAGONISTS .1. DETERMINATION OF THE RELATIVE AND ABSOLUTE STEREOCHEMICAL REQUIREMENTS [J].
HARRISON, T ;
WILLIAMS, BJ ;
SWAIN, CJ ;
BALL, RG .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (21) :2545-2550
[6]   ALPHA-HYDROXY KETONES IN HIGH ENANTIOMERIC PURITY FROM ASYMMETRIC DIHYDROXYLATION OF ENOL ETHERS [J].
HASHIYAMA, T ;
MORIKAWA, K ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5067-5068
[7]  
Hodgkinson TJ, 1998, SYNTHESIS-STUTTGART, P1141
[8]   ESTER ENOLATE CLAISEN REARRANGEMENT - STEREOCHEMICAL CONTROL THROUGH STEREOSELECTIVE ENOLATE FORMATION [J].
IRELAND, RE ;
MUELLER, RH ;
WILLARD, AK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) :2868-2877
[9]  
Swain CJ, 1998, PROGR MED CHEM, V35, P57, DOI 10.1016/S0079-6468(08)70034-1
[10]  
VAULTIER M, 1986, B SOC CHIM FR, P83