O-silyl triflate-promoted addition of diethyl phosphite to chiral aldonitrones.: A rapid access to complex α-amino phosphonates and their N-hydroxy derivatives

被引：22
作者：
De Risi, C
Dondoni, A
Perrone, D
Pollini, GP
机构：
[1] Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
[2] Univ Ferrara, Chim Organ Lab, Dipartimento Chim, I-44100 Ferrara, Italy
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 16期
关键词：
nitrones; phosphonates; enzyme inhibitors; peptide mimetics; stereoselective synthesis; aminophosphonation;
D O I：
10.1016/S0040-4039(01)00363-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The addition reaction of diethyl phosphite to O-silylated N-benzyl nitrones derived from chiral alpha -alkoxy and N-Boc alpha -amino aldehydes has been studied as a stereoselective carbon-phosphorus bond forming process for the synthesis of polyhydroxylated alpha -amino and alpha,beta -diamino phosphonates. Key intermediates are the corresponding N-hydroxy alpha -amino phosphonates. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3033 / 3036
页数：4
相关论文
共 24 条
[1]   TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE-PROMOTED CYCLOADDITION OF NITRONES WITH SILYL ENOL ETHERS - SYNTHESIS AND REACTIVITY OF 5-SILOXYISOXAZOLIDINES [J].
CAMILETTI, C ;
DHAVALE, DD ;
GENTILUCCI, L ;
TROMBINI, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (24) :3157-3165
[2]   STEREOCONTROL BY DIETHYLALUMINUM CHLORIDE IN THE ADDITION OF 2-LITHIOFURAN AND N-METHYL-2-LITHIOIMIDAZOLE TO ALPHA-ALKOXY NITRONES - TOTAL SYNTHESIS OF 5-O-CARBAMOYLPOLYOXAMIC ACID [J].
DONDONI, A ;
FRANCO, S ;
MERCHAN, FL ;
MERINO, P ;
TEJERO, T .
TETRAHEDRON LETTERS, 1993, 34 (34) :5479-5482
[3]   New entry to pyrrolidine homoazasugars: conversion of D-arabinose into 2,5-anhydro-2,5-imino-D-glucitol via aminohomologation [J].
Dondoni, A ;
Perrone, D .
TETRAHEDRON LETTERS, 1999, 40 (52) :9375-9378
[4]   STEREOSELECTIVE HOMOLOGATION - AMINATION OF ALDEHYDES BY ADDITION OF THEIR NITRONES TO C-2 METALATED THIAZOLES - A GENERAL ENTRY TO ALPHA-AMINO ALDEHYDES AND AMINO-SUGARS [J].
DONDONI, A ;
FRANCO, S ;
JUNQUERA, F ;
MERCHAN, FL ;
MERINO, P ;
TEJERO, T ;
BERTOLASI, V .
CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (08) :505-520
[5]  
DONDONI A, 1994, SYNTHESIS-STUTTGART, P1450
[6]   Grignard addition to aldonitrones.: Stereochemical aspects and application to the synthesis of C2-symmetric diamino alcohols and diamino diols [J].
Dondoni, A ;
Perrone, D ;
Rinaldi, M .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9252-9264
[7]   SYNTHESIS OF N-BENZYL NITRONES [J].
DONDONI, A ;
FRANCO, S ;
JUNQUERA, F ;
MERCHAN, F ;
MERINO, P ;
TEJERO, T .
SYNTHETIC COMMUNICATIONS, 1994, 24 (18) :2537-2550
[8]  
Dondoni A, 1997, ALDRICHIM ACTA, V30, P35
[9]   Applications of sugar nitrones in synthesis: The total synthesis of (+)-polyoxin J [J].
Dondoni, A ;
Franco, S ;
Junquera, F ;
Merchan, FL ;
Merino, P ;
Tejero, T .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5497-5507
[10]   N-hydroxy-alpha-amino phosphonate derivatives as potential haptens for eliciting catalytic antibodies [J].
Gouverneur, V ;
Lalloz, MN .
TETRAHEDRON LETTERS, 1996, 37 (35) :6331-6334
123