A short and practical access to both enantiomers of 4-hydroxycyclohexenone based on a desymmetrizing CBS reduction

被引：17

作者：

Nising, Carl F. ^{[1
]}

Ohnemueller, Ulrike K. ^{[1
]}

Braese, Stefan ^{[1
]}

机构：

[1] Univ Karlsruhe, Inst Organ Chem, D-76131 Karlsruhe, Germany

来源：

SYNTHESIS-STUTTGART | 2006年 / 16卷 / 16期

关键词：

asymmetric catalysis; oxazaborolidines; cyclohexenones; reduction; desymmetrization;

D O I：

10.1055/s-2006-942484

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By employing an unprecedented CBS-catalyzed reductive desymmetrization of the readily available meso-diketone 2, both enantiomers of the cyclohexenone precursor 3 can be synthesized in up to 92% yield and 98% ee. From this precursor, 4-hydroxycyclohexenone (1) is easily liberated by a retro Diels-Alder reaction.

引用

页码：2643 / 2645

页数：3

共 27 条

[1]

[Anonymous], ANGEW CHEM

[2]

[Anonymous], 1997, ANGEW CHEM

[3] SYNTHESIS OF 2 USEFUL, ENANTIOMERICALLY PURE DERIVATIVES OF (S)-4-HYDROXY-2-CYCLOHEXENONE [J].

AUDIA, JE ;

BOISVERT, L ;

PATTEN, AD ;

VILLALOBOS, A ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3738-3740

[4]

BACKVALL JE, 1984, J ORG CHEM, V49, P4619

[5] CYCLOPENTADIENES AS CHIRAL TEMPLATES .4. AN EASY ACCESS TO (S)-HYDROXYCYCLOHEXENONE AND (R)-HYDROXYCYCLOHEXENONE [J].

BRUNJES, R ;

TILSTAM, U ;

WINTERFELDT, E .

CHEMISCHE BERICHTE, 1991, 124 (07) :1677-1678

[6]

CARRENO MC, 1990, TETRAHEDRON LETT, V31, P6653

[7]

COREY EJ, 1998, ANGEW CHEM, V110, P2092

[8] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[9] New, highly efficient syntheses of rac-, (R)- and (S)-4-hydroxy-2-cyclohexenone [J].

de March, P ;

Escoda, M ;

Figueredo, M ;

Font, J ;

García-García, E ;

Rodríguez, S .

TETRAHEDRON-ASYMMETRY, 2000, 11 (22) :4473-4483

[10] A new and efficient chemoenzymatic route to both enantiomers of 4-hydroxycyclohex-2-en-1-one [J].

Demir, AS ;

Sesenoglu, O .

ORGANIC LETTERS, 2002, 4 (12) :2021-2023

← 1 2 3 →