Kinetic resolution of citronellal by chiral aluminum catalysts: l-menthol synthesis from citral-Reference-Cited by-同舟云学术

Kinetic resolution of citronellal by chiral aluminum catalysts: l-menthol synthesis from citral

Published:2014 Issue:9 Volume:1 Page:1107-1115
ISSN:2052-4129
Container-title:Org. Chem. Front.
language:en
Short-container-title:Org. Chem. Front.

Author:

Itoh Hisanori¹²³⁴⁵,Maeda Hironori¹²,Yamada Shinya¹²,Hori Yoji¹²,Mino Takashi³⁴⁵⁶,Sakamoto Masami³⁴⁵⁶

Affiliation:

1. Taksasago International Corporation

2. Hiratsuka City, Japan

3. Department of Applied Chemistry and Biotechnology

4. Graduate School of Engineering

5. Chiba University

6. Inage-ku, Japan

Abstract

We developed a highly reactive catalytic ring-closing ene reaction with chiral aluminum complexes. Kinetic resolutions of citronellal successfully afforded 68% ee of diastereoselective isopulegol and 62% ee of citronellal at 47% conversion with the BINOL-Al catalyst. l-Menthol was synthesized from citral with kinetic resolutions.

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2014/QO/C4QO00222A

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