New silyl ether reagents for the absolute stereochemical determination of secondary alcohols

被引:16
|
作者
Williamson, RT
Sosa, ACB
Mitra, A
Seaton, PJ
Weibel, DB
Schroeder, FC
Meinwald, J
Koehn, FE
机构
[1] Wyeth Res, Pearl River, NY 10965 USA
[2] Manhattan Coll, Coll Mt St Vincent, Dept Chem, Bronx, NY 10471 USA
[3] Manhattan Coll, Coll Mt St Vincent, Dept Biochem, Bronx, NY 10471 USA
[4] Univ N Carolina, Dept Chem, Wilmington, NC 28403 USA
[5] Cornell Univ, Dept Chem & Biol Chem, Ithaca, NY 14853 USA
关键词
D O I
10.1021/ol034418o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Herein we report a new set of silyl ether reagents for determining the enantiomeric purity and absolute stereochemistry of secondary alcohols. These derivatives are easily synthesized, provide straightforward spectroscopic results, and allow for facile recovery of the original chiral alcohol.
引用
收藏
页码:1745 / 1748
页数:4
相关论文
共 50 条
  • [1] New silyl ether reagents for the absolute stereochemical determination of secondary alcohols. (vol 5, pg 1748, 2003)
    Williamson, RT
    Sosa, ACB
    Mitra, A
    Seaton, PJ
    Weibel, DB
    Schroeder, FC
    Meinwald, J
    Koehn, FE
    ORGANIC LETTERS, 2003, 5 (13) : 2371 - 2371
  • [2] CFTA, a new efficient agent for determination of absolute configurations of chiral secondary alcohols
    Takahashi, T
    Fukuishima, A
    Tanaka, Y
    Takeuchi, Y
    Kabuto, K
    Kabuto, C
    CHEMICAL COMMUNICATIONS, 2000, (09) : 787 - 788
  • [3] Chiral anisotropic reagents for determining the absolute configuration of secondary alcohols and carboxylic acids
    Kusumi, T
    Yabuuchi, T
    Takahashi, H
    Ooi, T
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2005, 63 (11) : 1102 - 1114
  • [4] New method for determining the absolute configuration of secondary alcohols
    Wagner, Alexander J.
    David, Jonathan G.
    Rychnovsky, Scott D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [5] Determination of absolute configuration of secondary alcohols using new chiral auxiliary and chemical shift calculation
    Iwamoto, H
    Kobayashi, Y
    Kawatani, T
    Suzuki, M
    Fukazawa, Y
    TETRAHEDRON LETTERS, 2006, 47 (10) : 1519 - 1523
  • [6] Monosaccharides as Potential Chiral Probes for the Determination of the Absolute Configuration of Secondary Alcohols
    Laskowski, Tomasz
    Szwarc, Katarzyna
    Szczeblewski, Pawel
    Sowinski, Pawel
    Borowski, Edward
    Pawlak, Jan
    JOURNAL OF NATURAL PRODUCTS, 2016, 79 (11): : 2797 - 2804
  • [7] Determination of absolute configurations of β- or γ-methyl substituted secondary alcohols by NMR spectroscopy
    Takahashi, H
    Iwashima, M
    Iguchi, K
    TETRAHEDRON LETTERS, 1999, 40 (02) : 333 - 336
  • [8] Determination of Absolute Configuration of Secondary Alcohols Using Thin-Layer Chromatography
    Wagner, Alexander J.
    Rychnovsky, Scott D.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (09): : 4594 - 4598
  • [9] Study for the determination of the absolute configuration of fluoromethylated secondary alcohols by the modified Mosher method
    Xiao, L
    Yamazaki, T
    Kitazume, T
    Yonezawa, T
    Sakamoto, Y
    Nogawa, K
    JOURNAL OF FLUORINE CHEMISTRY, 1997, 84 (01) : 19 - 23
  • [10] CHIRAL SILYL ACETALS AS CONVENIENT REAGENTS FOR DETERMINING ENANTIOMERIC PURITY OF ALCOHOLS
    CHAN, TH
    PENG, QJ
    WANG, D
    GUO, JA
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (05) : 325 - 326