Dramatic Substituent Effect on the CCL‐catalyzed Kinetic Resolution of 1‐Aryl‐2, 3‐allenols

Optically active I-aryl-2.3-allenols were obtained via CCL-mediated kinetic resolution of the racemic allenols. The substitution pattern of the aromatic rhg. regarding to both the type of the substituent and its position on the aromatic ring, was found to be critical for the kinetic resolution of l-aryl-2, 3-allenols.

[1]  S. Ma,et al.  Efficient preparation of highly optically active (S)-(-)-2,3-allenols and (R)-(+)-2,3-allenyl acetates by a clean novozym-435-catalyzed enzymatic separation of racemic 2,3-allenols. , 2002, Chemistry.

[2]  Shimin Zhao,et al.  Efficient synthesis of optically active 2,3-allenols via the simple CuBr-mediated reaction of optically active propargylic alcohols with paraformaldehyde , 2002 .

[3]  S. Ma,et al.  Efficient synthesis of 4-(2'-alkenyl)-2,5-dihydrofurans and 5,6-dihydro-2H-pyrans via the Pd-catalyzed cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides. , 2002, The Journal of organic chemistry.

[4]  Shimin Zhao,et al.  Novel Substituent and Chelating Effects in the Pd-Catalyzed Reaction of 2,3-Allenols, Aryl Iodides, and Amines. Highly Regio- and Stereoselective Synthesis of 2-Amino-3-alken-1-ols or 4-Amino-2(E)-alken-1-ols , 2001 .

[5]  S. Ma,et al.  Efficient synthesis of 4-(2′-alkenyl)-2,5-dihydrofurans via PdCl2-catalyzed coupling–cyclization reaction of 2,3-allenols with allylic halides , 2000 .

[6]  Zhang,et al.  Ruthenium-catalyzed cyclic carbonylation of allenyl alcohols. Selective synthesis of gamma- and delta-lactones , 2000, Organic letters.

[7]  赵士民,et al.  Pd(0)-catalyzed insertion-cyclization reaction of 2,3-allenols with aryl or alkenyl halides. Diastereoselective synthesis of highly optically active trans-2,3-disubstituted vinylic oxiranes. , 1999 .

[8]  L. Bieber,et al.  Zinc barbier reaction of propargyl halides in water , 1998 .

[9]  Tokutaro Yamaguchi,et al.  Palladium-catalyzed arylation of α-allenic alcohols with hypervalent iodonium salts: Synthesis of epoxides and diol cyclic carbonates , 1998 .

[10]  A. Ito,et al.  Carbonyl propargylation or allenylation by 3-haloprop-1-yne with tin(II) halides and tetrabutylammonium halides , 1998 .

[11]  J. A. Marshall,et al.  DIASTEREO- AND ENANTIOSELECTIVE SYNTHESIS OF ALLENYLCARBINOLS THROUGH SE2'ADDITION OF TRANSIENT NONRACEMIC PROPARGYLIC STANNANES TO ALDEHYDES , 1995 .

[12]  J. A. Marshall,et al.  Stereoselective synthesis of 2,5-dihydrofurans by sequential SN2' cleavage of alkynyloxiranes and silver(I)-catalyzed cyclization of the allenylcarbinol products , 1993 .

[13]  K. Burgess,et al.  Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp , 1991 .

[14]  Aviva Rappaport,et al.  A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa , 1991 .

[15]  K. Burgess,et al.  Kinetic resolutions of chiral unsaturated alcohols that cannot be resolved efficiently via enantioselective epoxidation , 1990 .

[16]  Xiang Gao,et al.  Reaction of Propargyl Bromide with Aldehydes in the Presence of Metallic Tin. Synthesis of Homopropargylalcohols and Homoallenylalcohols , 1990 .

[17]  M. Iyoda,et al.  Simple and Efficient Synthesis of α-Allenic Alcohols and Their Novel Conversion into 1-Aryl-3-formyloxy-1,3-butadienes , 1989 .

[18]  J. Schwab,et al.  Stereochemical Course of an Enzyme-Catalyzed Allene-Acetylene Isomerization. , 1986 .

[19]  J. B. Jones,et al.  Enantiomerically selective pig liver esterase-catalysed hydrolyses of racemic allenic esters , 1986 .

[20]  I. Shimizu,et al.  Facile synthesis of β-aryl- or β-alkenyl-β-methyl-α,β-unsaturated carbonyl compounds by palladium-catalyzed reaction of 1,2-dien-4-ols with aryl or alkenyl halides , 1985 .

[21]  T. Tam,et al.  Novel suicide inhibitors of serine proteinases. Inactivation of human leukocyte elastase by ynenol lactones , 1984 .

[22]  P. Casara,et al.  General synthetic access to α-allenyl amines and α-allenyl-α-aminoacids as potential enzyme activated irreversible inhibitors of PLP dependent enzymes , 1984 .

[23]  S. Patai.  Ketenes, Allenes and Related Compounds: Vol. 1 (1980) , 1980 .

[24]  L. Olsson,et al.  Synthesis of 2,5-Dihydrofurans and 5,6-Dihydro-2H-pyrans by Silver(I)-Catalyzed Cyclization of Allenic Alcohols , 1979 .

[25]  J. Luche,et al.  Efficient homologation of acetylenes to allenes , 1979 .