Synthesis of Optically Pure (R)- and (S)-Tetrahydroisoquinoline-1-and-3-Carboxylic Acids

被引：6

作者：

Kurata, Kaoruko ^{[1
]}

Inoue, Kumiko ^{[1
]}

Nishimura, Kazuhiko ^{[1
]}

Hoshiya, Naoyuki ^{[1
]}

Kawai, Nobuyuki ^{[2
]}

Uenishi, Jun'ichi ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Dept Pharmaceut Chem, Yamashina Ku, Kyoto 6078412, Japan

[2] Mukogawa Womens Univ, Sch Pharmaceut Sci, Nishinomiya, Hyogo 6638179, Japan

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 09期

关键词：

quinolines; amino acids; peptides; asymmetric synthesis; Lewis acids; 1,2,3,4-TETRAHYDROISOQUINOLINE-1-CARBOXYLIC ACID; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; AMINO-ACIDS; DERIVATIVES; CHEMISTRY; DESIGN;

D O I：

10.1055/s-0034-1380289

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (R)- and (S)-tetrahydroisoquinoline-1-carboxylic acids was achieved from N-Boc-protected (R)- and (S)-1-propenyltetrahydroisoquinoline, respectively, in a three-step sequence of ozonolysis, NaBH4 reduction, oxidation, and deprotection of the N-Boc group. Similarly, (S)-tetrahydroisoquinoline-3-carboxylic acids were obtained from N-Boc-protected (S)-3-(4-phenylbutenyl) tetrahydroisoquinolines. This synthetic route provides tetrahydroisoquinoline ring-based cyclic amino acids in enantiomerically pure form in a practical and efficient manner.

引用

页码：1238 / 1244

页数：7

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