STEREOSELECTIVE DEUTERATION OF A BRIDGEHEAD POLYCYCLIC 2-NITRO ALCOHOL THROUGH A RETRO-HENRY REACTION

被引：5

作者：

CAMPS, P

MUNOZTORRERO, D

MUNOZTORRERO, V

机构：

[1] Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, E-08028 Barcelona, Av. Diagonal s/n

来源：

TETRAHEDRON | 1995年 / 51卷 / 23期

关键词：

D O I：

10.1016/0040-4020(95)00296-K

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of nitro alcohol 2a with the stoichiometric amount of NaOH in water or D2O gave ketonitronate 3a or 3c, respectively. In CD3OD or CH3OH solution It room temperature, 3a and 3c gave cleanly the dideuterated derivatives 3b and 3d, respectively. Treatment of 3a-d with acetic acid gave the corresponding polycyclic nitro alcohols 2a-d.

引用

页码：6587 / 6590

页数：4

共 5 条

[1] Camps, Munoz-Torrero, Tetrahedron Lett., 35, pp. 3187-3190, (1994)
[2] Camps, Font-Bardia, Munoz-Torrero, Solans, Synthesis of bridgehead polycyclic 1,2-diamines and 2-amino alcohol derivatives as Rigid acetylcholine analogs, Liebigs Annalen, pp. 523-535, (1995)
[3] Bowman, Golding, Watson, The structures of nitronate salts in solution as determined by 13C and 1H n.m.r. spectroscopy, Journal of the Chemical Society, Perkin Transactions 2, pp. 731-736, (1980)
[4] Begbie, Bowman, Golding, Watson, Special effects in nuclear magnetic resonance spectra of nitronate anions, Journal of the Chemical Society, Chemical Communications, pp. 645-646, (1974)
[5] Deslongchamps, Stereoelectronic Effects in Organic Chemistry, pp. 274-284, (1983)

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