A new method for preparation of 3,6-dihydro-2H-1,3-oxazines and explorations of their use in stereoselective synthesis of 1,3-amino alcohol derivatives

被引：14

作者：

Cherkauskas, JP

Klos, AM

Borzilleri, RM

Sisko, J

Weinreb, SM

Parvez, M

机构：

[1] PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802

[2] UNIV CALGARY,DEPT CHEM,CALGARY,AB T2N 1N4,CANADA

来源：

TETRAHEDRON | 1996年 / 52卷 / 09期

关键词：

D O I：

10.1016/0040-4020(95)01100-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of P-hydroxy aldehydes with N-sulfonyl aldimines produces 3,6-dihydro-2H-1,3-oxazines in moderate to excellent yields. The process is stereoselective, with the C-2 and C-6 substituents having a trans relationship in these heterocycles. Some transformations of these oxazines as potential acyclic 1,3-amino alcohol synthons are described.

引用

收藏

页码：3135 / 3152

页数：18

相关论文

共 30 条

[1]

ADAM W, 1991, CHEM BER, V124, P237

[2] CARBON-CARBON BOND FORMATION VIA N-TOSYLIMINIUM IONS [J].

AHMAN, J ;

SOMFAI, P .

TETRAHEDRON, 1992, 48 (43) :9537-9544

[3]

AHMAN J, 1992, TETRAHEDRON LETT, V33, P3791

[4] HETEROCYCLEN DURCH DIENSYNTHESE .2. N-[BUTYLOXYCARBONYLMENTHYLEN]-P-TOLUOLSULFONAMID EIN NEUES DIENOPHIL ZUR DARSTELLUNG VON PYRIDIN- PIPERIDEIN- UND PIPERIDIN-DERIVATEN DURCH DIELS-ALDER-SYNTHESE [J].

ALBRECHT, R ;

KRESZE, G .

CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (05) :1431-&

[5] ARYLSULFONYLIMINE - DARSTELLUNG EIGENSCHAFTEN UND REAKTIVITAT [J].

ALBRECHT, R ;

KRESZE, G ;

MLAKAR, B .

CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (02) :483-&

[6]

ALDER B, 1978, J PRAKT CHEM, P904

[7] A GENERAL-METHOD FOR THE REDUCTIVE CARBAMATION AND SULFONAMIDATION OF ALDEHYDES [J].

ALEXANDER, MD ;

ANDERSON, RE ;

SISKO, J ;

WEINREB, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2563-2564

[8] STEREOSELECTIVE SYNTHESIS OF 1,3-AMINO ALCOHOLS AND 1,3-AMINO KETONES [J].

BARLUENGA, J ;

AGUILAR, E ;

FUSTERO, S ;

OLANO, B ;

VIADO, AL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1219-1223

[9] 1,3-AMINO ALCOHOLS FROM 4-AMINO-1-AZA DIENES - DIASTEREOSELECTIVE AND ENANTIOSELECTIVE APPROACH TO THE 4 DIASTEREOISOMERS OF THE N-TERMINAL AMINO-ACID COMPONENT OF NIKKOMYCIN-B AND NIKKOMYCIN-B(X) [J].

BARLUENGA, J ;

VIADO, AL ;

AGUILAR, E ;

FUSTERO, S ;

OLANO, B .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5972-5975

[10] CONVENIENT PROCEDURE FOR THE REDUCTION OF BETA-ENAMINO KETONES - SYNTHESIS OF GAMMA-AMINO ALCOHOLS AND TETRAHYDRO-1,3-OXAZINES [J].

BARTOLI, G ;

CIMARELLI, C ;

PALMIERI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (05) :537-543