anti-1,2-diols via Ni-catalyzed reductive coupling of alkynes and α-oxyaldehydes

被引：55
作者：
Luanphaisarnnont, T [1 ]
Ndubaku, CO [1 ]
Jamison, TF [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 14期
关键词：
D O I：
10.1021/ol050881k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiornerically enriched alpha-oxyaldehydes (2) afford differentiated anti-1,2-diols (3) with high diastereoselectivity and regioselectivity, despite the fact that the methoxymethyl (MOM) and para-methoxybenzyl (PMB) protective groups typically favor syn-1,2-diol formation in carbonyl addition reactions of this family of aldehydes.
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页码：2937 / 2940
页数：4
相关论文
共 33 条
  • [1] HIGH DIASTEREOFACE SELECTION IN AN ESTER ENOLATE ADDITION TO ALPHA-ALKOXY ALDEHYDES - STEREOSELECTIVE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS
    BANFI, L
    BERNARDI, A
    COLOMBO, L
    GENNARI, C
    SCOLASTICO, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20) : 3784 - 3790
  • [2] RABBIT MUSCLE ALDOLASE AS A CATALYST IN ORGANIC-SYNTHESIS
    BEDNARSKI, MD
    SIMON, ES
    BISCHOFBERGER, N
    FESSNER, WD
    KIM, MJ
    LEES, W
    SAITO, T
    WALDMANN, H
    WHITESIDES, GM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) : 627 - 635
  • [3] CHELATES AS INTERMEDIATES IN NUCLEOPHILIC ADDITIONS TO ALKOXY KETONES ACCORDING TO CRAM RULE (CYCLIC MODEL)
    CHEN, XN
    HORTELANO, ER
    ELIEL, EL
    FRYE, SV
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1778 - 1784
  • [4] P-chiral, monodentate ferrocenyl phosphines, novel ligands for asymmetric catalysis
    Colby, EA
    Jamison, TF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (01) : 156 - 166
  • [5] A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES
    COREY, EJ
    YU, CM
    KIM, SS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5495 - 5496
  • [6] STUDIES IN STEREOCHEMISTRY .10. THE RULE OF STERIC CONTROL OF ASYMMETRIC INDUCTION IN THE SYNTHESES OF ACYCLIC SYSTEMS
    CRAM, DJ
    ELHAFEZ, FAA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (23) : 5828 - 5835
  • [7] Anti-selective aldol reactions with titanium enolates of N-glycolyloxazolidinethiones
    Crimmins, MT
    McDougall, PJ
    [J]. ORGANIC LETTERS, 2003, 5 (04) : 591 - 594
  • [8] ELIEL EL, 1983, ASYMMETRIC SYNTHESIS, V2, P125
  • [9] ASYMMETRIC-SYNTHESIS OF CALYCULIN-A .2. THE C-26-C-37 GAMMA-AMINO ACID FRAGMENTS
    EVANS, DA
    GAGE, JR
    LEIGHTON, JL
    KIM, AS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) : 1961 - 1963
  • [10] ENZYMES IN ORGANIC-SYNTHESIS .1. DIASTEREOSELECTIVE ENZYMATIC ALDOL ADDITIONS - L-RHAMNULOSE AND L-FUCULOSE 1-PHOSPHATE ALDOLASES FROM ESCHERICHIA-COLI
    FESSNER, WD
    SINERIUS, G
    SCHNEIDER, A
    DREYER, M
    SCHULZ, GE
    BADIA, J
    AGUILAR, J
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05): : 555 - 558
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