Toward the development of a structurally novel class of chiral auxiliaries:: Diastereoselective aldol reactions of a (1R,2S)-ephedrine-based 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one

被引：40

作者：

Casper, DM ^{[1
]}

Burgeson, JR ^{[1
]}

Esken, JM ^{[1
]}

Ferrence, GM ^{[1
]}

Hitchcock, SR ^{[1
]}

机构：

[1] Illinois State Univ, Dept Chem, Normal, IL 61790 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 21期

关键词：

D O I：

10.1021/ol026721f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] Asymmetric aldol addition reactions have been conducted with (1R,2S)-ephedrine-derived 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one (2). Diastereoselectivities range from 75:25 to 99:1 for the formation of the crude non-Evans syn adducts 8a-h. The facial selectivity of the enolate is directed by the stereogenic N-4-methyl substituent. Aldol adduct 8a is readily cleaved by acid hydrolysis to afford (2S,3s)-3-hydroxy-2-methyl-3-phenylpropionic acid (9) in >95% ee.

引用

收藏

页码：3739 / 3742

页数：4

相关论文

共 48 条

[1]

Ager DJ, 1997, ALDRICHIM ACTA, V30, P3

[2] Asymmetric total synthesis of (+)-tolterodine, a new muscarinic receptor antagonist, via copper-assisted asymmetric conjugate addition of aryl Grignard reagents to 3-phenyl-prop-2-enoyl-oxazolidinones [J].

Andersson, PG ;

Schink, HE ;

Österlund, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :8067-8070

[3] Toward the development of a general chiral auxiliary.: Part 6:: Structural effects on diastereoselection using camphor derived lactams:: evaluation of (1R,4S)-1,7,7-trimethyl-3-azabicyclo[2.2.1]hept-5-en-3-one as a chiral controller [J].

Boeckman, RK ;

Laci, MA ;

Johnson, AT .

TETRAHEDRON-ASYMMETRY, 2001, 12 (02) :205-217

[4] TOWARD THE DEVELOPMENT OF A GENERAL CHIRAL AUXILIARY .3. DESIGN AND EVALUATION OF A NOVEL CHIRAL BICYCLIC LACTAM FOR ASYMMETRIC ALDOL CONDENSATIONS - EVIDENCE FOR THE IMPORTANCE OF DIPOLE ALIGNMENT IN THE TRANSITION-STATE [J].

BOECKMAN, RK ;

CONNELL, BT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (49) :12368-12369

[5] Synthesis of N4-substituted[1,3,4]oxadiazinan-2-ones derived from norephedrine [J].

Casper, DM ;

Nora, GP ;

Blackburn, JR ;

Bentley, JT ;

Taylor, DC ;

Hitchcock, SR .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (04) :823-828

[6] Asymmetric Diels-Alder, Michael, and Aldol reactions using a planar chiral 1,3-oxazol-2(3H)-one derived from (R)-(+)-4-hydroxy-[2.2]paracyclophane [J].

Cipiciani, A ;

Fringuelli, F ;

Piermatti, O ;

Pizzo, F ;

Ruzziconi, R .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2665-2670

[7] Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones [J].

Crimmins, MT ;

King, BW ;

Tabet, EA ;

Chaudhary, K .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :894-902

[8] ASYMMETRIC ALDOL AND ALKYLATION REACTIONS MEDIATED BY THE QUAT CHIRAL AUXILIARY (R)-(-)-5-METHYL-3,3-DIMETHYL-2-PYRROLIDINONE [J].

DAVIES, SG ;

DOISNEAU, GJM ;

PRODGER, JC ;

SANGANEE, HJ .

TETRAHEDRON LETTERS, 1994, 35 (15) :2373-2376

[9] BIFUNCTIONAL CHIRAL AUXILIARIES .7. ALDOL REACTIONS OF ENOLATES DERIVED FROM 1,3-DIACYLIMIDAZOLIDINE-2-THIONES AND 1,3-DIACYLIMIDAZOLIDIN-2-ONES [J].

DAVIES, SG ;

EDWARDS, AJ ;

EVANS, GB ;

MORTLOCK, AA .

TETRAHEDRON, 1994, 50 (22) :6621-6642

[10]

de Parrodi CA, 2001, TETRAHEDRON-ASYMMETR, V12, P69

← 1 2 3 4 5 →