Enantioselective photochemical reactions of 2-pyridones in solution

被引：58

作者：

Bach, T ^{[1
]}

Bergmann, H ^{[1
]}

Harms, K ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 04期

关键词：

D O I：

10.1021/ol007004t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Two key photochemical reactions of prochiral 2-pyridones were studied in the presence of a chiral host. The [4 + 4]-photocycloaddition with cyclopentadiene (CpH) proceeded smoothly and with high enantioselectivity (84-87% eel. The absolute configuration of the endo-diastereoisomer was established by Xray crystallography. The electrocyclic [4 pi]-ring closure to 3-oxo-2-azabicyclo[2.2.0]-5-hexenes occurred with lower enantioselectivity (20-23% ee at -20 degreesC). The velocity of the latter reaction slowed significantly with decreasing temperature.

引用

页码：601 / 603

页数：3

共 27 条

[1] Hydroxy-directed regio- and diastereoselective [2+2] photocycloaddition (Paterno-Buchi reaction) of benzophenone to chiral allylic alcohols [J].

Adam, W ;

Peters, K ;

Peters, EM ;

Stegmann, VR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) :2958-2959

[2] Enantioselective intermolecular [2+2]-photocycloaddition reactions of alkenes and a 2-quinolone in solution [J].

Bach, T ;

Bergmann, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) :11525-11526

[3] High facial diastereoselectivity in the photocycloaddition of a chiral aromatic aldehyde and an enamide induced by intermolecular hydrogen bonding [J].

Bach, T ;

Bergmann, H ;

Harms, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (45) :10650-10651

[4]

Bach T, 2000, ANGEW CHEM INT EDIT, V39, P2302, DOI 10.1002/1521-3773(20000703)39:13<2302::AID-ANIE2302>3.0.CO

[5]

2-6

[6] Supramolecular catalysis of olefin [2+2] photodimerization [J].

Bassani, DM ;

Darcos, V ;

Mahony, S ;

Desvergne, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (36) :8795-8796

[7] INTERNAL PHOTOADDITION REACTIONS OF 2-PYRONE + N-METHYL-2-PYRIDONE - NEW SYNTHETIC APPROACH TO CYCLOBUTADIENE [J].

COREY, EJ ;

STREITH, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (05) :950-&

[8] Solvent effects on diastereoselective intramolecular [2+2] photocycloadditions: Reversal of selectivity through intramolecular hydrogen bonding [J].

Crimmins, MT ;

Choy, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (42) :10237-10238

[9]

DESALMS RD, 1972, TETRAHEDRON LETT, P3563

[10]

Dilling, 1976, ORG PHOTOCHEM SYNTH, V2, P5

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