Stereoselectivity of triplet photocycloadditions, part 10 -: Oxazole-Carbonyl photocycloadditions:: selectivity pattern and synthetic route to erythro α-amino, β-hydroxy ketones

被引:32
作者
Griesbeck, AG [1 ]
Fiege, M [1 ]
Lex, J [1 ]
机构
[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
关键词
D O I
10.1039/b000578i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The photocycloaddition of aliphatic and aromatic aldehydes with 2,4,5-trimethyloxazole proceeds highly regio- and diastereoselectively to give bicyclic oxetanes; hydrolytic cleavage of these adducts gives selectively erythro alpha-amino, beta-hydroxy methyl ketones.
引用
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页码:589 / 590
页数:2
相关论文
共 15 条
[1]  
Bach T, 1997, LIEBIGS ANN-RECL, P1627
[2]   Facial diastereoselectivity in the photocycloaddition of chiral N-acyl enamines to benzaldehyde [J].
Bach, T ;
Schröder, J ;
Brandl, T ;
Hecht, J ;
Harms, K .
TETRAHEDRON, 1998, 54 (18) :4507-4520
[3]   Photocycloaddition of N-acyl enamines to aldehydes and its application to the synthesis of diastereomerically pure 1,2-amino alcohols [J].
Bach, T ;
Schröder, J .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1265-1273
[4]  
Bach T, 1998, SYNTHESIS-STUTTGART, P683
[5]  
Griesbeck A. G., UNPUB
[6]   INTERSYSTEM CROSSING IN TRIPLET 1,4-BIRADICALS - CONFORMATIONAL MEMORY EFFECTS ON THE STEREOSELECTIVITY OF PHOTOCYCLOADDITION REACTIONS [J].
GRIESBECK, AG ;
MAUDER, H ;
STADTMULLER, S .
ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (03) :70-75
[7]   ELECTRONIC CONTROL OF STEREOSELECTIVITY IN PHOTOCYCLOADDITION REACTIONS .4. EFFECTS OF METHYL SUBSTITUENTS AT THE DONOR OLEFIN [J].
GRIESBECK, AG ;
STADTMULLER, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :6923-6928
[8]   PHOTOCYCLOADDITION OF BENZALDEHYDE TO CYCLIC OLEFINS - ELECTRONIC CONTROL OF ENDO STEREOSELECTIVITY [J].
GRIESBECK, AG ;
STADTMULLER, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) :1281-1283
[9]   Stereoselectivity of triplet photocycloadditions: Diene-carbonyl reactions and solvent effects [J].
Griesbeck, AG ;
Buhr, S ;
Fiege, M ;
Schmickler, H ;
Lex, J .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :3847-3854
[10]  
GRIESBECK AG, 1995, HDB ORGANIC PHOTOCHE, P550