Practical synthesis of Boc and Fmoc protected 4-fluoro and 4-difluoroprolines from trans-4-hydroxyproline

被引：73
作者：
Demange, L [1 ]
Ménez, A [1 ]
Dugave, C [1 ]
机构：
[1] CEA Saclay, Dept Ingn Etud Prot, F-91191 Gif Sur Yvette, France
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 10期
关键词：
D O I：
10.1016/S0040-4039(97)10793-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Boc-cis-4-fluoro-L-proline and 4-difluoro-L-proline, usable in classical peptide synthesis, were obtained in respectively 71% (3 steps) and 65% (4 steps) overall yields from the readily available trans-4-hydroxy-L-proline methyl ester. The corresponding fluorinated Irans-isomer was isolated in 24% yield (5 steps). Transformation of Boc-protected compounds to their Fmoc-equivalents was performed in high yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码：1169 / 1172
页数：4
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