Synthesis and oxidative reactivity of new chiral hypervalent iodine(V) reagents based on (S)-proline

被引:72
作者
Ladziata, Uladzimir [1 ]
Carlson, Jeffrey [1 ]
Zhdankin, Viktor V. [1 ]
机构
[1] Univ Minnesota, Dept Chem & Biochem, Duluth, MN 55812 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/j.tetlet.2006.06.103
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Design and preparation of two chiral pseudo-benziodoxazine derivatives based on inexpensive and readily available (S)-proline have been carried out. The evaluation of these new reagents as stereoselective oxidizing agents toward a racemic alcohol, meso-diol, and sulfide was performed. Moderate enantio selectivities in a range of 29-41% have been achieved. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6301 / 6304
页数:4
相关论文
共 42 条
[31]   Synthesis and oxidation reactions of a user- and eco-friendly hypervalent iodine reagent [J].
Thottumkara, AP ;
Vinod, TK .
TETRAHEDRON LETTERS, 2002, 43 (04) :569-572
[32]   Hypervalent iodine reagents for the oxidation of alcohols and their application to complex molecule synthesis [J].
Tohma, H ;
Kita, Y .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :111-124
[33]   Hypervalent iodine(V)-induced asymmetric oxidation of sulfides to sulfoxides mediated by reversed micelles: Novel nonmetallic catalytic system [J].
Tohma, H ;
Takizawa, S ;
Watanabe, H ;
Fukuoka, Y ;
Maegawa, T ;
Kita, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3519-3523
[34]  
Tohma H, 2000, CHEM PHARM BULL, V48, P445
[36]   Chiral hypervalent iodine compounds [J].
Wirth, T ;
Hirt, UH .
TETRAHEDRON-ASYMMETRY, 1997, 8 (01) :23-26
[37]  
Wirth T., 2003, Hypervalent Iodine Chemistry: Modern Developments in Synthesis
[38]   Esters of 2-iodoxybenzoic acid: Hypervalent iodine oxidizing reagents with a pseudobenziodoxole structure [J].
Zhdankin, VV ;
Koposov, AY ;
Litvinov, DN ;
Ferguson, MJ ;
McDonald, R ;
Luu, T ;
Tykwinski, RR .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6484-6491
[39]   Benziodoxole-based hypervalent iodine reagents in organic synthesis [J].
Zhdankin, VV .
CURRENT ORGANIC SYNTHESIS, 2005, 2 (01) :121-145
[40]   Preparation and structure of 2-iodoxybenzoate esters: soluble and stable periodinane oxidizing reagents [J].
Zhdankin, VV ;
Litvinov, DN ;
Koposov, AY ;
Luu, T ;
Ferguson, MJ ;
McDonald, R ;
Tykwinski, RR .
CHEMICAL COMMUNICATIONS, 2004, (01) :106-107