Hydroxy group directivity in the epoxidation of chiral allylic alcohols: Control of diastereoselectivity through allylic strain and hydrogen bonding

被引：155

作者：

Adam, W ^{[1
]}

Wirth, T ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 1999年 / 32卷 / 08期

关键词：

D O I：

10.1021/ar9800845

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

[No abstract available]

引用

页码：703 / 710

页数：8

共 43 条

[1] Adam W, 1999, EUR J ORG CHEM, V1999, P785
[2] A highly diastereoselective dioxetane formation by the hydroxy-directed [2+2] cycloaddition of singlet oxygen to a chiral allylic alcohol
Adam, W
Saha-Möller, CR
Schambony, SB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) : 1834 - 1838
[3] HYDROXY-DIRECTED REGIOSELECTIVE AND DIASTEREOSELECTIVE ENE REACTION OF SINGLET OXYGEN WITH CHIRAL ALLYLIC ALCOHOLS
ADAM, W
NESTLER, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5041 - 5049
[4] (Z)-3-METHYL-3-PENTEN-2-OL AS STEREOCHEMICAL PROBE FOR 1,2 VERSUS 1,3 ALLYLIC STRAIN IN THE PHOTOOXYGENATION AND EPOXIDATION OF CHIRAL ALLYLIC ALCOHOLS
ADAM, W
NESTLER, B
[J]. TETRAHEDRON LETTERS, 1993, 34 (04) : 611 - 614
[5] pi-Facial diastereoselectivity in the [4+2] cycloaddition of singlet oxygen as a mechanistic probe
Adam, W
Prein, M
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) : 275 - 283
[6] Methyltrioxorhenium(VII)-catalyzed epoxidation of alkenes with the urea hydrogen peroxide adduct
Adam, W
Mitchell, CM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (05): : 533 - 535
[7] Diastereoselective catalytic epoxidation of chiral allylic alcohols by the TS-1 and Ti-beta zeolites: Evidence for a hydrogen-bonded, peroxy-type loaded complex as oxidizing species
Adam, W
Corma, A
Reddy, TI
Renz, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) : 3631 - 3637
[8] Synthesis of optically active α-hydroxy carbonyl compounds by the catalytic, enantioselective oxidation of silyl enol ethers and ketene acetals with (salen)manganese(III) complexes
Adam, W
Fell, RT
Stegmann, VR
Saha-Möller, CR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) : 708 - 714
[9] Adam W, 1997, LIEBIGS ANN-RECL, P1365
[10] Solvent effects in the regio- and diastereoselective epoxidations of acyclic allylic alcohols by dimethyldioxirane: Hydrogen bonding as evidence for a dipolar transition state
Adam, W
Smerz, AK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) : 3506 - 3510

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