ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS VIA THE ZINC-MEDIATED GLYCINE ESTER ENOLATE IMINE CONDENSATION REACTION USING ALPHA-AMINO ESTERS AS THE CHIRAL AUXILIARY

被引:18
作者
VANMAANEN, HL
KLEIJN, H
JASTRZEBSKI, JTBH
VERWEIJ, J
KIEBOOM, APG
VANKOTEN, G
机构
[1] UNIV UTRECHT,DEBYE RES INST,DEPT MET MEDIATED SYNTH,3584 CH UTRECHT,NETHERLANDS
[2] GIST BROCADES,RES & DEV,2600 MA DELFT,NETHERLANDS
关键词
D O I
10.1021/jo00119a009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Imine esters of glycine, (R)-phenylglycine, (R)-(1,4-cyclohexadienyl)glycine and (S)-valine have been employed in the ester enolate-imine condensation via double activation with ZnCl2. The reaction of the chlorozinc enolate (1b) of ethyl (2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)acetate with (R)-methyl N-benzylidene-2-phenylglycinate (2a) afforded the trans-beta-lactam 3a in 79% yield with excellent asymmetric induction (de >97%). Other imine esters also afforded trans-beta-lactams diastereoselectively, albeit in lower conversions (37-70%). Methyl (S)-2-[N-[3-(trimethylsilyl)-2-propyn-1-ylidene]amino]-3-methylbutanoate (2e) afforded a mixture of four diastereoisomers (68% conversion). The products were isolated as 3-phthalimido beta-lactams 5b-e and as 3-[(methoxycarbonyl)amino]-beta-lactam 6b. The reactivity of the zinc enolates and the diastereoselectivity of the reactions are discussed in terms of the coordination of the imine esters to ZnCl2 (template effect) and the stability and aggregation equilibria of the zinc enolates.
引用
收藏
页码:4331 / 4338
页数:8
相关论文
共 99 条
  • [1] SYNTHESIS OF NOVEL FUNCTIONALIZED MONOCYCLIC 2-AZETIDINONES FROM N,N'-DIARYL-ALPHA-DIIMINES AND LITHIUM ESTER ENOLATES
    ALCAIDE, B
    GOMEZ, A
    PLUMET, J
    RODRIGUEZLOPEZ, J
    [J]. TETRAHEDRON, 1989, 45 (09) : 2751 - 2762
  • [2] THE STEREOSELECTIVE PREPARATION OF MONO-BETA-LACTAMS AND BIS-BETA-LACTAMS BY THE 1,4-DIAZA 1,3-DIENE-ACID CHLORIDE CONDENSATION - SCOPE AND SYNTHETIC APPLICATIONS
    ALCAIDE, B
    MARTINCANTALEJO, Y
    PEREZCASTELLS, J
    RODRIGUEZLOPEZ, J
    SIERRA, MA
    MONGE, A
    PEREZGARCIA, V
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) : 5921 - 5931
  • [3] STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES BEARING A CHIRAL AUXILIARY
    ANNUNZIATA, R
    BENAGLIA, M
    CINQUINI, M
    COZZI, F
    RAIMONDI, L
    [J]. TETRAHEDRON LETTERS, 1993, 34 (43) : 6921 - 6924
  • [4] SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF THE TIN ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES - A COMPARISON BETWEEN TITANIUM AND TIN ENOLATES
    ANNUNZIATA, R
    BENAGLIA, M
    CINQUINI, M
    COZZI, F
    RAIMONDI, L
    [J]. TETRAHEDRON, 1994, 50 (19) : 5821 - 5828
  • [5] STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYL THIOESTERS WITH IMINES
    ANNUNZIATA, R
    CINQUINI, M
    COZZI, F
    COZZI, PG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) : 4155 - 4162
  • [6] STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYL THIOESTERS WITH IMINES BEARING A CHIRAL AUXILIARY
    ANNUNZIATA, R
    BENAGLIA, M
    CINQUINI, M
    COZZI, F
    RAIMONDI, L
    [J]. TETRAHEDRON, 1994, 50 (31) : 9471 - 9486
  • [7] HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY ADDITION OF TITANIUM ENOLATES OF 2-PYRIDYL THIOESTERS TO CHIRAL IMINES
    ANNUNZIATA, R
    CINQUINI, M
    COZZI, F
    COZZI, PG
    [J]. TETRAHEDRON LETTERS, 1992, 33 (08) : 1113 - 1116
  • [8] REAGENTS AND SYNTHETIC METHODS .67. PREPARATION OF 4-UNSUBSTITUTED BETA-LACTAMS FROM 4-ACETOXYAZETIDIN-2-ONES - A FORMAL APPROACH TO MONOBACTAMS AND NOCARDINCINS
    ARRIETA, A
    LECEA, B
    COSSIO, FP
    PALOMO, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) : 3784 - 3791
  • [9] REMOVAL OF SULFUR-PROTECTING GROUPS IN SYNTHESIS OF A 4-MERCAPTO-BETA-LACTAM
    BACHI, MD
    ROSSPETE.KJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (01) : 12 - 13
  • [10] STUDIES RELATED TO PENICILLINS AND CEPHALOSPORINS .2. APPROACH TO SYNTHESIS OF BETA-LACTAM ANTIBIOTICS
    BACHI, MD
    GOLDBERG, O
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (18): : 2332 - &