NORPSEUDOEPHEDRINE-DERIVED 2-METHOXY-3-SULFONYL-1,3-OXAZOLIDINES - CHIRAL, HIGHLY DIASTEREOSELECTIVE FORMYL CATION EQUIVALENTS

被引：25

作者：

CONDEFRIEBOES, K ^{[1
]}

HOPPE, D ^{[1
]}

机构：

[1] CHRISTIAN ALBRECHTS UNIV KIEL,INST ORGAN CHEM,OLSHAUSENSTR 40,W-2300 KIEL 1,GERMANY

来源：

TETRAHEDRON | 1992年 / 48卷 / 29期

关键词：

2-METHOXY-1,3-OXAZOLIDINE; ENANTIOSELECTIVE FORMYLATION; CHIRAL; 2-FORMYLCYCLOALKANONES;

D O I：

10.1016/S0040-4020(01)89849-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2S,4R 5R)-2-Methoxy-4-methyl-3-(4-methylbenzenesulfonyl)-5-phenyl-1,3-oxazolidine (2c) adds trimethylsilyl 1-cycloalkenyl ethers under Lewis acid catalysis with complete induced and high simple diastereoselectivity to yield homochiral oxazolidine-masked 2-formylalkanones.

引用

页码：6011 / 6020

页数：10

共 12 条

[1]

[Anonymous], 1989, ANGEW CHEM, V101, P65

[2] NOREPHEDRINE DERIVED 2-METHOXY OXAZOLIDINES AS CHIRAL FORMYL CATION EQUIVALENTS [J].

BERNARDI, A ;

CARDANI, S ;

CARUGO, O ;

COLOMBO, L ;

SCOLASTICO, C ;

VILLA, R .

TETRAHEDRON LETTERS, 1990, 31 (19) :2779-2782

[3] ASYMMETRIC-SYNTHESIS OF MALIC ACID-TYPE SYNTHONS VIA CHIRAL NOREPHEDRINE-DERIVED OXAZOLIDINES [J].

BERNARDI, A ;

CARDANI, S ;

SCOLASTICO, C ;

VILLA, R .

TETRAHEDRON, 1990, 46 (06) :1987-1998

[4]

BERNARDI A, 1992, TETRAHEDRON, V40, P1343

[5] A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS .1. FROM SIMPLE ALDEHYDES AND KETONES [J].

CAZEAU, P ;

DUBOUDIN, F ;

MOULINES, F ;

BABOT, O ;

DUNOGUES, J .

TETRAHEDRON, 1987, 43 (09) :2075-2088

[6] PREPARATION OF BETA-KETO ESTER ACETALS BY REACTION OF ORTHO ESTERS WITH KETENE SILYL ACETALS IN THE PRESENCE OF TITANIUM TETRACHLORIDE [J].

COLLINS, DJ ;

CHOO, GLP ;

OBRIST, H .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (03) :617-622

[7]

CONDEFRIEBOES K, 1990, SYNLETT, P99

[8] ASYMMETRIC ALDOL ADDITION-REACTIONS OF A CHIRAL 3-SULFONYL-1,3-OXAZOLIDINE-MASKED LITHIUM 2-FORMYLCYCLOHEXANONE ENOLATE [J].

HOPPE, I ;

HOPPE, D ;

HERBSTIRMER, R ;

EGERT, E .

TETRAHEDRON LETTERS, 1990, 31 (47) :6859-6862

[9] 3-ARYLSULFONYLOXAZOLIDINES AS CHIRAL TEMPLATES - ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED 2-HYDROXYCYCLOHEXANECARBALDEHYDES FROM 2-HYDROXYMETHYLENECYCLOHEXANONE [J].

HOPPE, I ;

HOPPE, D ;

WOLFF, C ;

EGERT, E ;

HERBST, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (01) :67-69

[10]

HOPPE I, 1991, SYNTHESIS-STUTTGART, P1157

← 1 2 →