Asymmetric synthesis of 2-substituted piperidines using a multi-component coupling reaction:: rapid assembly of (S)-coniine from (S)-1-(1-phenylethyl)-2-methyleneaziridine

被引:45
作者
Hayes, JF
Shipman, M [1 ]
Twin, H
机构
[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England
[2] GlaxoSmithKline, Tonbridge TN11 9AN, Kent, England
关键词
D O I
10.1039/b106260n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(S)-Coniine is made using a reaction which assembles the piperidine ring by the sequential formation of four new chemical bonds and installs the C-2 stereogenic centre with high levels of diastereocontrol (90% de).
引用
收藏
页码:1784 / 1785
页数:2
相关论文
共 24 条
[1]   Asymmetric routes to substituted piperidines [J].
Bailey, PD ;
Millwood, PA ;
Smith, PD .
CHEMICAL COMMUNICATIONS, 1998, (06) :633-640
[2]   A new asymmetric synthesis of (S)-(+)-pipecoline and (S)-(+)- and (R)-(-)-coniine by reductive photocyclization of dienamides [J].
Bois, F ;
Gardette, D ;
Gramain, JC .
TETRAHEDRON LETTERS, 2000, 41 (45) :8769-8772
[3]   AMINES DERIVED FROM DIHALOPROPENES .2. SYNTHESIS OF (+/-)-1-(2-METHYLENE-1-AZIRIDINYL)-3-BUTEN-2-OL AND (-)-1-(2-METHYLENE-L-AZIRIDINYL))-3-BUTEN-2-OL [J].
BOTTINI, AT ;
DEV, V .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (03) :968-&
[4]   Convenient in situ synthesis of nonracemic N-protected β-amino aldehydes from β-amino acids.: Applications in Wittig reactions and heterocycle synthesis [J].
Davies, SB ;
McKervey, MA .
TETRAHEDRON LETTERS, 1999, 40 (06) :1229-1232
[5]  
ENDERS D, 1993, LIEBIGS ANN CHEM, P173
[6]  
Eskici M, 2000, SYNLETT, P1360
[7]   The United Kingdom Chemical Database Service [J].
Fletcher, DA ;
McMeeking, RF ;
Parkin, D .
JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 1996, 36 (04) :746-749
[8]  
Hammann P., 1995, ORGANIC SYNTHESIS HI, P323
[9]   Generation of metalloenamines by carbon-carbon bond formation: ring opening reactions of 2-methyleneaziridines with organometallic reagents [J].
Hayes, JF ;
Shipman, M ;
Twin, H .
CHEMICAL COMMUNICATIONS, 2000, (18) :1791-1792
[10]  
Hirai Y, 1998, J SYN ORG CHEM JPN, V56, P50