Enantioselective synthesis of cyclic sulfamidates via Pd-catalyzed hydrogenation

被引：139
作者：
Wang, You-Qing [1 ]
Yu, Chang-Bin [1 ]
Wang, Da-Wei [1 ]
Wang, Xiao-Bing [1 ]
Zhou, Yong-Gui [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 10期
关键词：
D O I：
10.1021/ol800591u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Using Pd(CF3CO2)(2)/(SS)-f-binaphane as the catalyst, an efficient enantioselective synthesis of cyclic sulfamidates was developed via asymmetric hydrogenation of the corresponding cyclic imines in 2,2,2-trifluoroethanol at room temperature with high enantioselectivities (up to 99% ee).
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收藏
页码：2071 / 2074
页数：4
相关论文
共 87 条
[1]   Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives [J].
Abe, H ;
Amii, H ;
Uneyama, K .
ORGANIC LETTERS, 2001, 3 (03) :313-315
[2]   Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: Application to the synthesis of thiooligosaccharides [J].
Aguilera, B ;
FernandezMayoralas, A .
CHEMICAL COMMUNICATIONS, 1996, (02) :127-128
[3]  
Alvaro G, 2002, SYNLETT, P651
[4]   1,2,3-BENZOXATHIAZOLE 2,2-DIOXIDES - SYNTHESIS, MECHANISM OF HYDROLYSIS, AND REACTIONS WITH NUCLEOPHILES [J].
ANDERSEN, KK ;
BRAY, DD ;
CHUMPRADIT, S ;
CLARK, ME ;
HABGOOD, GJ ;
HUBBARD, CD ;
YOUNG, KM .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6508-6516
[5]   ACIDITY OF CYCLIC SULFAMATES - STUDY OF SUBSTITUTED 1,2,3-BENZOXATHIAZOLE 2,2-DIOXIDES AND THEORETICAL INVESTIGATION OF THE EFFECT OF CONFORMATION ON ACIDITY [J].
ANDERSEN, KK ;
KOCIOLEK, MG .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2003-2007
[6]   N-(9-(9-phenylfluorenyl))homoserine-derived cyclic sulfamidates:: Novel chiral educts for the synthesis of enantiopure γ-substituted α-amino acids [J].
Atfani, M ;
Wei, L ;
Lubell, WD .
ORGANIC LETTERS, 2001, 3 (19) :2965-2968
[7]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[8]   Cyclic sulfamidates as vehicles for the synthesis of substituted lactams [J].
Bower, JF ;
Svenda, J ;
Williams, AJ ;
Charmant, JPH ;
Lawrence, RM ;
Szeto, P ;
Gallagher, T .
ORGANIC LETTERS, 2004, 6 (25) :4727-4730
[9]   Cyclic sulfamidates as precursors to alkylidene pyrrolidines and piperidines [J].
Bower, John F. ;
Szeto, Peter ;
Gallagher, Timothy .
ORGANIC LETTERS, 2007, 9 (23) :4909-4912
[10]   Enantiopure 1,4-benzoxazines via 1,2-cyclic sulfamidates. Synthesis of levofloxacin [J].
Bower, John F. ;
Szeto, Peter ;
Gallagher, Timothy .
ORGANIC LETTERS, 2007, 9 (17) :3283-3286
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