Concise synthesis of enantiomerically pure phenylalanine, homophenylalanine, and bishomophenylalanine derivatives using organozinc chemistry: NMR studies of amino acid-derived organozinc reagents

被引：109

作者：

Jackson, RFW

Moore, RJ

Dexter, CS

Elliot, J

Mowbray, CE

机构：

[1] Univ Newcastle Upon Tyne, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

[2] Merck Sharp & Dohme Res Labs, Neurosci Res Ctr, Harlow CM20 2QR, Essex, England

[3] Pfizer Ltd, Dept Discovery Chem, Sandwich CT13 9NJ, Kent, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 22期

关键词：

D O I：

10.1021/jo981133u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Protected phenylalanines 23 (seven examples), homophenylalanines 7 (eight examples), and bishomophenylalanines 8 (seven examples) have been prepared by palladium-catalyzed coupling of the amino acid-derived organozinc reagents 13, 5, and 6, respectively, with aryl iodides. While the reactions of the zinc reagent 13 may be conducted in both THF and DMF as solvent, the results obtained in DMF are generally superior. In the case of the reagents 5 and 6 the results are far superior in DMF. NMR investigations on the structure of the zinc reagents 13 in THF suggest that there is strong intramolecular coordination of the urethane carbonyl group, whereas in DMF this interaction is completely suppressed.

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页码：7875 / 7884

页数：10

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