Special Issue

Keiichiro Fukumoto's Special Issues, Vol. 77, No. 1, 2009

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Note | Special issue | Vol 77, No. 1, 2009, pp. 629 - 634
Published online: 21st August, 2008
DOI: 10.3987/COM-08-S(F)46
Highly Stereoselective Synthesis of (2R,3R)-2-Amino-3-cyclohexyl-3-hydroxypropionic Acid Using Asymmetric Hydrogenation

Kazuishi Makino, Takayuki Goto, Junpei Ohtaka, and Yasumasa Hamada*

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


(2R,3R)-2-Amino-3-cyclohexyl-3-hydroxypropionic acid, a α-hydroxy-β-amino acid in a new CCR5 antagonist, was efficiently synthesized by the Noyori asymmetric hydrogenation of α-benzoylamino-β-keto ester (6) and intramolecular SN2-type inversion as the key steps.

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Note | Special issue | Vol 77, No. 1, 2009, pp. 635 - 644
Published online: 28th August, 2008
DOI: 10.3987/COM-08-S(F)61
Modified 3-Hydroxypipecolic Acid Derivatives as an Organocatalyst

Yuichi Yoshimura, Chiaki Ohara, Tatsunori Miyagawa, and Hiroki Takahata*

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


Novel 3-hydroxypipecolic acid derivatives were synthesized from glycine by using the method we developed previously. Among the 3-hydroxypipecolic acid derivatives obtained, a 2,3-trans-3-O-TBDPS-4,5-didehydro derivative showed the most promising result as an asymmetric catalyst in the Mannich reaction of ethyl 4-(methoxyphenylimino)acetate and n-hexylaldehyde.

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