D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective aldol reactions

被引：30

作者：

Lutzen, A ^{[1
]}

Koll, P ^{[1
]}

机构：

[1] UNIV OLDENBURG,DEPT CHEM,ORGAN CHEM LAB,D-26111 OLDENBURG,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(97)00096-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral N-acylated oxazolidin-2-one derivatives from D-xylose have been shown to undergo diastereoselective aldol reactions via their lithium imide enolates to afford beta-hydroxylated products. Aliphatic substrates and aldehydes were shown to yield 'non-Evans' syn-aldols readily interpreted by assuming chelated chair-like transition states. When substrates and aldehydes bearing aromatic groups are used chelated boat- or twist-boat-like transition states seem to become similarly or even more probable so that anti- or syn-aldols are also formed from cis- or trans-enolates, respectively. (C) 1997 Elsevier Science Ltd.

引用

页码：1193 / 1206

页数：14

共 51 条

[11] Asymmetric Diels-Alder reactions employing modified camphor-derived oxazolidin-2-one chiral auxiliaries [J].

Banks, MR ;

Blake, AJ ;

Cadogan, JIG ;

Doyle, AA ;

Gosney, I ;

Hodgson, PKG ;

Thorburn, P .

TETRAHEDRON, 1996, 52 (11) :4079-4094

[12] ASYMMETRIC ALDOL REACTIONS - A NEW CAMPHOR-DERIVED CHIRAL AUXILIARY GIVING HIGHLY STEREOSELECTIVE ALDOL REACTIONS OF BOTH LITHIUM AND TITANIUM(IV) ENOLATES [J].

BONNER, MP ;

THORNTON, ER .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1299-1308

[13]

ELIEL EL, 1994, STEREOCHEMISTRY ORGA, P897

[14] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC IONOMYCIN [J].

EVANS, DA ;

DOW, RL ;

SHIH, TL ;

TAKACS, JM ;

ZAHLER, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5290-5313

[15] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256

[16] TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC RUTAMYCIN-B [J].

EVANS, DA ;

NG, HP ;

RIEGER, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11446-11459

[17] CHIRAL ENOLATE DESIGN [J].

EVANS, DA ;

TAKACS, JM ;

MCGEE, LR ;

ENNIS, MD ;

MATHRE, DJ ;

BARTROLI, J .

PURE AND APPLIED CHEMISTRY, 1981, 53 (06) :1109-1127

[18] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[19] CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA .

TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144

[20]

GAGE JR, 1989, ORG SYNTH, V68, P77

← 1 2 3 4 5 6 →