Base assisted substitution of α-amidoalkyl sulfones by nitromethane anion.: A new entry to functionalized α-amino acids.

被引：37

作者：

Ballini, R ^{[1
]}

Petrini, M ^{[1
]}

机构：

[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 23期

关键词：

amino acids and derivatives; nitrocompounds; sulfones;

D O I：

10.1016/S0040-4039(99)00770-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nitromethane anion reacts with alpha-amidoalkyl sulfones in THF affording the corresponding nitro derivatives that upon oxidation with alkaline potassium permanganate give the corresponding N-protected a-amino acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4449 / 4452

页数：4

共 23 条

[1] Beller M, 1998, CHEM-EUR J, V4, P935, DOI 10.1002/(SICI)1521-3765(19980515)4:5<935::AID-CHEM935>3.0.CO
[2] 2-#
[3] SUBSTITUTION-REACTIONS OF 2-BENZENESULFONYL CYCLIC ETHERS WITH CARBON NUCLEOPHILES
BROWN, DS
BRUNO, M
DAVENPORT, RJ
LEY, SV
[J]. TETRAHEDRON, 1989, 45 (13) : 4293 - 4308
[4] CINCHILLA R, 1997, RECENT RES DEV ORGAN, V1, P437
[5] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS
DUTHALER, RO
[J]. TETRAHEDRON, 1994, 50 (06) : 1539 - 1650
[6] Enders D, 1996, SYNTHESIS-STUTTGART, P1443
[7] SUBSTITUTION-REACTIONS WHICH PROCEED VIA RADICAL-ANION INTERMEDIATES
KORNBLUM, N
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (11): : 734 - 745
[8] Highly stereoselective conjugate addition of (R)- or (S)-4-Phenyl-2-oxazolidinone to nitroalkenes
Lucet, D
Toupet, L
LeGall, T
Mioskowski, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) : 2682 - 2683
[9] Novel transformation of primary nitroalkanes and primary alkyl bromides to the corresponding carboxylic acids
Matt, C
Wagner, A
Mioskowski, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) : 234 - 235
[10] UNUSUAL CHEMOSELECTIVITY AND STEREOSELECTIVITY IN THE ADDITION OF CHIRAL AMINOALCOHOLS TO ACHIRAL NITROALKENES
MORRIS, ML
STURGESS, MA
[J]. TETRAHEDRON LETTERS, 1993, 34 (01) : 43 - 46

← 1 2 3 →