Carboxylate-stabilised sulfur ylides (thetin salts) in asymmetric epoxidation for the synthesis of glycidic acids. Mechanism and implications.

作者: Varinder K. Aggarwal , Christina Hebach

DOI: 10.1039/B418740G

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摘要: … Excellent yields of the trans-substituted glycidic esters could be obtained with a wide range of … employing potassium ylides was not realised (Table 3, entry 4, 5), as the potassium ylides …

参考文章(33)
Ryukichi Takagi, Jyunji Kimura, Yoshihiro Shinohara, Yuko Ohba, Kyoko Takezono, Yoshikazu Hiraga, Satoshi Kojima, Katsuo Ohkata, Asymmetric induction in Darzens condensation by means of (−)-8-phenylmenthyl and (−)-menthyl auxiliaries Journal of the Chemical Society, Perkin Transactions 1. pp. 689- 698 ,(1998) , 10.1039/A707310K
Kjell Sjöberg, Stable solutions of methylsulfinyl carbanion Tetrahedron Letters. ,vol. 7, pp. 6383- 6384 ,(1966) , 10.1016/S0040-4039(00)70182-1
A. G. Howard, D. W. Russell, Borohydride-Coupled HPLC-FPD Instrumentation and Its Use in the Determination of Dimethylsulfonium Compounds. Analytical Chemistry. ,vol. 69, pp. 2882- 2887 ,(1997) , 10.1021/AC970167J
Enrico G Baggiolini, Bernard M Hennessy, Jerome A Iacobelli, Milan R Uskokovic, Stereospecific synthesis of the lythgoe's ring a aldehyde for the preparation of 1α-hdroxylated tachysterols and calciferols Tetrahedron Letters. ,vol. 28, pp. 2095- 2098 ,(1987) , 10.1016/S0040-4039(00)96052-0
Varinder K. Aggarwal, Jonathan P. H. Charmant, Cinzia Ciampi, Jonathan M. Hornby, Christopher J. O'Brien, George Hynd, Richard Parsons, Additions of stabilised and semi-stabilised sulfur ylides to tosyl protected imines: are they under kinetic or thermodynamic control? Journal of The Chemical Society-perkin Transactions 1. pp. 3159- 3166 ,(2001) , 10.1039/B107275G
Varinder K. Aggarwal, Jeremy N. Harvey, Jeffery Richardson, Unraveling the Mechanism of Epoxide Formation from Sulfur Ylides and Aldehydes Journal of the American Chemical Society. ,vol. 124, pp. 5747- 5756 ,(2002) , 10.1021/JA025633N
Varinder K. Aggarwal, George Hynd, Willy Picoul, Jean-Luc Vasse, Highly enantioselective darzens reaction of a camphor-derived sulfonium amide to give glycidic amides and their applications in synthesis. Journal of the American Chemical Society. ,vol. 124, pp. 9964- 9965 ,(2002) , 10.1021/JA0272540
Ying-Chuan Wang, Chi-Lung Li, Hsi-Liang Tseng, Shang-Chi Chuang, Tu-Hsin Yan, An efficient method for the synthesis of enantiopure cis-α,β-epoxy acids Tetrahedron-asymmetry. ,vol. 10, pp. 3249- 3251 ,(1999) , 10.1016/S0957-4166(99)00320-1
Masao Shiozaki, Noboru Ishida, Sadao Sato, Synthesis of 2-Amino-2-deoxy-α-D-altrofuranoside Derivatives from 2,3-O-Isopropylidene-D-glyceraldehyde via Bicyclic β-Lactam Intermediates Bulletin of the Chemical Society of Japan. ,vol. 62, pp. 3950- 3958 ,(1989) , 10.1246/BCSJ.62.3950