[Bis(2-methoxyethyl)amino]sulfur trifluoride, the deoxo-fluor reagent: Application toward one-flask transformations of carboxylic acids to amides

被引:57
作者
White, JM [1 ]
Tunoori, AR [1 ]
Turunen, BJ [1 ]
Georg, GI [1 ]
机构
[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA
关键词
D O I
10.1021/jo035658k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of the Deoxo-Fluor reagent is a versatile method for acyl fluoride generation and subsequent one-flask amide coupling. It provides mild conditions and facile purification of the desired products in good to excellent yields. We have explored the utility of this reagent for the one-flask conversion of acids to amides and Weinreb amides and as a peptide-coupling reagent.
引用
收藏
页码:2573 / 2576
页数:4
相关论文
共 32 条
[1]   ALPHA-DIKETONE AND ALPHA-KETO ESTER DERIVATIVES OF N-PROTECTED AMINO-ACIDS AND PEPTIDES AS NOVEL INHIBITORS OF CYSTEINE AND SERINE PROTEINASES [J].
ANGELASTRO, MR ;
MEHDI, S ;
BURKHART, JP ;
PEET, NP ;
BEY, P .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :11-13
[2]   EFFICIENT PREPARATION OF PEPTIDYL PENTAFLUOROETHYL KETONES [J].
ANGELASTRO, MR ;
BURKHART, JP ;
BEY, P ;
PEET, NP .
TETRAHEDRON LETTERS, 1992, 33 (23) :3265-3268
[3]   AMINO-ACID FLUORIDES - THEIR PREPARATION AND USE IN PEPTIDE-SYNTHESIS [J].
BERTHO, JN ;
LOFFET, A ;
PINEL, C ;
REUTHER, F ;
SENNYEY, G .
TETRAHEDRON LETTERS, 1991, 32 (10) :1303-1306
[4]  
BRAUN M, 1989, SYNTHESIS-STUTTGART, P856
[5]   BIS(BOC) AMINO-ACID FLUORIDES AS REACTIVE PEPTIDE COUPLING REAGENTS [J].
CARPINO, LA ;
MANSOUR, ESME ;
EL-FAHAM, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :4162-4164
[6]   ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID FLUORIDES - CONVENIENT NEW PEPTIDE COUPLING REAGENTS APPLICABLE TO THE FMOC/TERT-BUTYL STRATEGY FOR SOLUTION AND SOLID-PHASE SYNTHESES [J].
CARPINO, LA ;
SADATAALAEE, D ;
CHAO, HG ;
DESELMS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9651-9652
[7]   Peptide synthesis via amino acid halides [J].
Carpino, LA ;
Beyermann, M ;
Wenschuh, H ;
Bienert, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) :268-274
[8]   TETRAMETHYLFLUOROFORMAMIDINIUM HEXAFLUOROPHOSPHATE - A RAPID-ACTING PEPTIDE COUPLING REAGENT FOR SOLUTION AND SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
EL-FAHAM, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (19) :5401-5402
[9]   TERT-BUTYLOXYCARBONYL AND BENZYLOXYCARBONYL AMINO-ACID FLUORIDES - NEW, STABLE RAPID-ACTING ACYLATING AGENTS FOR PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
MANSOUR, EME ;
SADATAALAEE, D .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2611-2614
[10]   A stereoselective synthesis of a C-glycosylated peptoid building block [J].
Dechantsreiter, MA ;
Burkhart, F ;
Kessler, H .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :253-254