Synthesis of α-fluorosulfonamides by electrophilic fluorination

被引:43
作者
Hill, B [1 ]
Yong, L [1 ]
Taylor, SD [1 ]
机构
[1] Univ Waterloo, Dept Chem, Waterloo, ON N2L 3G1, Canada
关键词
D O I
10.1021/ol048249z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-Fluorosulfonamides were prepared by electrophilic fluorination of tertiary sulfonamides using N-fluorobenzenesulfonimide as fluorinating agent and utilizing the dimethoxybenzyl group (DMB) as a new sulfonamide protecting group. Removal of the DMB group with TFA/CH2Cl2 gave primary and secondary alpha-fluorosulfonamides.
引用
收藏
页码:4285 / 4288
页数:4
相关论文
共 16 条
[1]   Evidence for the mechanism of the irreversible inhibition of oestrone sulphatase (ES) by aminosulphonate based compounds [J].
Ahmed, S ;
Owen, CP ;
James, K ;
Patel, CK ;
Sampson, L .
JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2002, 80 (4-5) :429-440
[2]  
BOWMAN WC, 1979, TXB PHARM, pCH34
[3]   Synthesis and reactivity of polydisulfonimides [J].
Burlingham, BT ;
Widlanski, TS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (13) :2937-2945
[4]  
DIFFERDING E, 1991, SYNLETT, P395
[5]  
HARRINGTON JK, 1970, J MED CHEM, V22, P137
[6]  
KATRITZKY AR, 1991, SYNTHESIS-STUTTGART, P703
[7]   Preparation of benzylic α,α-difluoronitriles, -tetrazoles, and -sulfonates via electrophilic fluorination [J].
Kotoris, CC ;
Chen, MJ ;
Taylor, SD .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :8052-8057
[8]   Practical synthesis of sultams via sulfonamide dianion alkylation: Application to the synthesis of chiral sultams [J].
Lee, JM ;
Zhong, YL ;
Reamer, RA ;
Askin, D .
ORGANIC LETTERS, 2003, 5 (22) :4175-4177
[9]   The difluoromethylenesulfonic acid group as a monoanionic phosphate surrogate for obtaining PTP1B inhibitors [J].
Leung, C ;
Grzyb, J ;
Lee, J ;
Meyer, N ;
Hum, G ;
Jia, CG ;
Liu, SF ;
Taylor, SD .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (07) :2309-2323
[10]   Synthesis of protected L-4-[sulfono(difluoromethyl)]phenylalanine and its incorporation into a peptide [J].
Liu, SF ;
Dockendorff, C ;
Taylor, SD .
ORGANIC LETTERS, 2001, 3 (10) :1571-1574