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O-(α-Phenylethyl)hydroxylamine as a ‘chiral ammonia equivalent’: synthesis and resolution of 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids |
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| Authors: | Ihor Kleban Andriy V Tymtsunik Yuliya V Rassukana Oleksandr O Grygorenko |
| Institution: | 1. National Taras Shevchenko University of Kyiv, Volodymyrska Street, 60, Kyiv 01601, Ukraine;3. National Technical University of Ukraine ‘Igor Sikorsky Kyiv Polytechnic Institute’, Prospect Peremogy 37, Kyiv 03056, Ukraine;4. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv 02094, Ukraine |
| Abstract: | An approach to the synthesis and resolution of five- and six-membered lactams (i.e., 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids) is described. The method relies on the one-pot Michael reaction—cyclization of itaconic acid or diethyl homoitaconate and enantiopure O-(α-phenylethyl)hydroxylamine as a ‘chiral ammonia equivalent’. It is shown that this chiral auxiliary can be used for the separation of diastereomeric lactam products and then easily removed by catalytic hydrogenolysis. |
| Keywords: | Corresponding author Tel : +38 044 239 33 15 fax: +38 044 502 48 32 |
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