ASYMMETRIC INDUCTION IN MANGANESE(III)-BASED OXIDATIVE FREE-RADICAL CYCLIZATIONS OF CHIRAL ESTERS AND AMIDES

被引：39

作者：

SNIDER, BB

ZHANG, QW

机构：

[1] Department of Chemistry Brandeis University, Waltham, MA 02254

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 40期

关键词：

D O I：

10.1016/S0040-4039(00)61089-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mn(III)-based oxidative free-radical cyclizations of phenylmenthyl acetoacetate 1d affords 90% of 11 with 86% de. trans-2-Phenylcyclohexyl ester 1e affords 5e with only 60% de. The 2,5-dimethylpyrrolidine amide 1h affords 14 with higher de (92%), but in only 28% yield.

引用

页码：5921 / 5924

页数：4

共 16 条

[1] HIGHLY DIASTEREOSELECTIVE ADDITION-REACTIONS OF A RADICAL DERIVED FROM A BETA-ETHOXYCARBONYL SULFOXIDE
BECKWITH, ALJ
HERSPERGER, R
WHITE, JM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (17) : 1151 - 1152
[2] STEREOGENIC REACTIONS OF THE ALPHA-CARBON RADICALS OF 8-PHENYLMENTHYL ESTERS
CHEN, MY
FANG, JM
TSAI, YM
YEH, RL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (22) : 1603 - 1604
[3] COREY EJ, 1979, TETRAHEDRON LETT, P399
[4] MANGANESE(III)-BASED OXIDATIVE FREE-RADICAL TANDEM AND TRIPLE CYCLIZATIONS
DOMBROSKI, MA
KATES, SA
SNIDER, BB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) : 2759 - 2767
[5] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES
EVANS, DA
BARTROLI, J
SHIH, TL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) : 2127 - 2129
[6] DECARBOXYLATION OF BETA-KETO ACIDS .2. AN INVESTIGATION OF BREDT RULE IN BICYCLO[3.2.1]OCTANE SYSTEMS
FERRIS, JP
MILLER, NC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (15) : 3522 - &
[7] ASYMMETRIC INDUCTION IN RADICAL REACTIONS - ENANTIOSELECTIVE SYNTHESES OF (S)-2-DEUTERIOGLYCINE AND (R)-2-DEUTERIOGLYCINE
HAMON, DPG
RAZZINO, P
MASSYWESTROPP, RA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) : 332 - 333
[8] ENANTIOSELECTIVE SYNTHESES OF ALPHA-AMINO-ACIDS VIA CARBON-CARBON BOND FORMING RADICAL REACTIONS
HAMON, DPG
MASSYWESTROPP, RA
RAZZINO, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (10) : 722 - 724
[9] HOUSE HO, 1972, MODERN SYNTHETIC REA, P514
[10] MANGANESE(III)-BASED OXIDATIVE FREE-RADICAL CYCLIZATION OF UNSATURATED BETA-KETO-ESTERS, 1,3-DIKETONES, AND MALONATE DIESTERS
KATES, SA
DOMBROSKI, MA
SNIDER, BB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) : 2427 - 2436

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