SYNTHESIS OF N-BOC-PROTECTED 1-AMINO-3-ALKEN-2-OLS FROM ALLYLIC CARBAMATES VIA PALLADIUM(II)-CATALYZED OXIDATIVE CYCLIZATION

被引:54
作者
VANBENTHEM, RATM [1 ]
HIEMSTRA, H [1 ]
SPECKAMP, WN [1 ]
机构
[1] UNIV AMSTERDAM,DEPT ORGAN CHEM,NIEUWE ACHTERGRACHT 129,1018 WS AMSTERDAM,NETHERLANDS
关键词
D O I
10.1021/jo00049a001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methyl glyoxylate adducts of N-Boc-protected allylic amines cyclize in the presence of catalytic Pd(OAc)2 and excess Cu(OAc)2 in DMSO to 5-(1-alkenyl)-2-(methoxycarbonyl)oxazolidines. These heterocycles are readily converted to unsaturated N-Boc-protected beta-amino alcohols through anodic oxidation and mild hydrolysis.
引用
收藏
页码:6083 / 6085
页数:3
相关论文
共 22 条
[1]   SYNTHESIS OF OXAZOLIDIN-2-ONES USING CARBONATE ION ON A POLYMERIC SUPPORT [J].
CARDILLO, G ;
ORENA, M ;
SANDRI, S ;
TOMASINI, C .
TETRAHEDRON, 1985, 41 (01) :163-167
[2]   OXAZOLIDIN-2-ONES FROM ALLYLIC AMINES BY MEANS OF IODINE AND CARBONATE ANION ON POLYMERIC SUPPORT - A CONVENIENT SYNTHESIS OF (+/-)-PROPRANOLOL [J].
CARDILLO, G ;
ORENA, M ;
SANDRI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) :713-717
[3]   STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].
CARDILLO, G ;
ORENA, M .
TETRAHEDRON, 1990, 46 (10) :3321-3408
[4]   AN EFFICIENT, PALLADIUM-CATALYZED ROUTE TO PROTECTED ALLYLIC AMINES [J].
CONNELL, RD ;
REIN, T ;
AKERMARK, B ;
HELQUIST, P .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3845-3849
[5]   STEREOCHEMISTRY ASSOCIATED WITH THE ADDITION OF 2-(TRIMETHYLSILYL)THIAZOLE TO DIFFERENTIALLY PROTECTED ALPHA-AMINO ALDEHYDES - APPLICATIONS TOWARD THE SYNTHESIS OF AMINO-SUGARS AND SPHINGOSINES [J].
DONDONI, A ;
FANTIN, G ;
FOGAGNOLO, M ;
PEDRINI, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1439-1446
[6]   REDUCTIVE CYCLIZATION OF CARBON-CENTERED GLYCINE RADICALS - A NOVEL SYNTHETIC ROUTE TO CYCLIC ALPHA-AMINO-ACIDS [J].
ESCH, PM ;
HIEMSTRA, H ;
DEBOER, RF ;
SPECKAMP, WN .
TETRAHEDRON, 1992, 48 (22) :4659-4676
[7]   SYNTHESIS OF HOMOCHIRAL UNSATURATED 7-MEMBERED LACTAMS [J].
EVANS, PA ;
HOLMES, AB ;
RUSSELL, K .
TETRAHEDRON-ASYMMETRY, 1990, 1 (09) :593-596
[8]   STEREOSPECIFIC SYNTHESIS OF ACYCLIC UNSATURATED AMINO-ALCOHOLS - A NEW APPROACH TO THREO-SPHINGOSINE AND ERYTHRO-SPHINGOSINE [J].
GARIGIPATI, RS ;
WEINREB, SM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (13) :4499-4501
[9]  
GREHN L, 1987, SYNTHESIS-STUTTGART, P275
[10]   OSMIUM-CATALYZED VICINAL OXYAMINATION OF OLEFINS BY N-CHLORO-N-ARGENTOCARBAMATES [J].
HERRANZ, E ;
BILLER, SA ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (11) :3596-3598