Highly Diastereoselective Synthesis of 2-(1-N-Boc-aminoalkyl)thiazole-5-carboxylates by Reduction of tert-Butylsulfinyl Ketimines

被引：3

作者：

Magata, Takuji ^{[1
]}

Hirokawa, Yoshimi ^{[1
]}

Furokawa, Aya ^{[1
]}

Takeuchi, Kazuhisa ^{[1
]}

Ohtomo, Yoshiaki ^{[1
]}

Kino, Toshitaka ^{[1
]}

Kominami, Jun ^{[1
]}

Nakai, Yuto ^{[1
]}

Kitamura, Maria ^{[1
]}

Maezaki, Naoyoshi ^{[1
]}

机构：

[1] Osaka Ohtani Univ, Fac Pharm, 3-11-1 Nishikiori Kita, Tondabayashi, Osaka 5848540, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2018年 / 66卷 / 04期

关键词：

thiazole amino acid; N-tert-butylsulfinyl ketimine; L-Selectride; ASYMMETRIC-SYNTHESIS; BUTANESULFINYL IMINES; NATURAL-PRODUCTS; CYCLIC-PEPTIDES; AMINO-ACIDS; OXAZOLE; ISOXAZOL-5(2H)-ONES; BIOSYNTHESIS; METABOLITES; THIAZOLE;

D O I：

10.1248/cpb.c17-00907

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Positional isomers of naturally occurring peptide subunits were synthesized via highly diastereoselective reduction of tert-butylsulfinyl ketimines as a key reaction. While NaBH4, reduction of ketimines derived from 2-thiazolyl ketones afforded the (R-s,R)-isomer with moderate diastereoselectivity, L-Selectride reduction afforded the (R-s,S)-isomer as the sole product. In contrast, ketimines derived from tert-butyl 2-thiazolyl ketone afforded the (R-s,R)-isomer with low diastereoselectivity by both NaBII, and L-Selectride reduction. Stereo chemistry of the reaction was discussed based on calculation of the conformational energies for ketimines.

引用

页码：416 / 422

页数：7

共 42 条

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