1,4-hydrogen radical transfer as a new and versatile tool for the synthesis of enantiomerically pure 1,2,3-triols

被引:37
作者
Gulea, M [1 ]
López-Romero, JM [1 ]
Fensterbank, L [1 ]
Malacria, M [1 ]
机构
[1] Univ Paris 06, CNRS, Lab Chim Organ Synth, F-75252 Paris 05, France
关键词
D O I
10.1021/ol000133p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] 1,4-Hydrogen radical transfers can now be reliably envisaged in radical synthetic chemistry as demonstrated by the formation of the cyano derivative II from I. Due to related sequences involving this new translocation process, followed by a highly diastereoselective trapping of the resulting anomeric radical, access to intriguing enantiopure 1,2,3-triols such as III is available.
引用
收藏
页码:2591 / 2594
页数:4
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[31]   RING-OPENING OF A FORMAL CYCLOPENTYLMETHYL RADICAL IN THE THERMOLYSIS OF DI(TERT-ALKYL)(1-NORBORNYL)METHANOLS [J].
LOMAS, JS ;
BRIAND, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (02) :191-200
[32]  
LUNAZZI L, 1987, J CHEM SOC P2, P703
[33]   Efficient synthesis of α-aldopyranosyl cyanides via radical cyanation reactions [J].
Martin, J ;
Jaramillo, LM ;
Wang, PG .
TETRAHEDRON LETTERS, 1998, 39 (33) :5927-5930
[34]   Stereoselective hydrogen transfer reactions of vinyl radicals: Cyclization of alkynyl iodides by unimolecular chain transfer from silicon hydrides [J].
MartinezGrau, A ;
Curran, DP .
TETRAHEDRON, 1997, 53 (16) :5679-5698
[35]   Rearrangements and cyclizations in vinyl radicals. Unusual example of 1,4-radical translocation. [J].
Montevecchi, PC ;
Navacchia, ML .
TETRAHEDRON LETTERS, 1996, 37 (36) :6583-6586
[36]  
NEALE RS, 1971, SYNTH-INT J METHODS, P1
[37]   Cyclopropanation by tandem radical [2+1] cycloaddition conducted by nickel complexes catalyzed electroreduction [J].
Ozaki, S ;
Matsui, E ;
Waku, J ;
Ohmori, H .
TETRAHEDRON LETTERS, 1997, 38 (15) :2705-2708
[38]   Alkylation of remote non-activated δ-carbon atoms:: Addition of δ-carbon radicals, generated by 1,5-hydrogen transfer in alkoxy radical intermediates, to activated olefins [J].
Petrovic, G ;
Cekovic, Z .
TETRAHEDRON, 1999, 55 (05) :1377-1390
[39]  
POLO C, 1991, HETEROCYCLES, V32, P1757
[40]   The synthesis of (+/-)-heliotridane and (6S,7S)-dihydroxyheliotridane via sequential hydrogen atom abstraction and cyclisation [J].
Robertson, J ;
Peplow, MA ;
Pillai, J .
TETRAHEDRON LETTERS, 1996, 37 (32) :5825-5828