An Efficient Petasis Boronic–Mannich Reaction of Chiral Lactol Derivatives Prepared from d-Araboascorbic Acid

Hiroki Mandai; Hiroshi Yamada; Keita Shimowaki; Koichi Mitsudo; Seiji Suga

doi:10.1055/s-0034-1378900

Synthesis, Table of Contents

Synthesis 2014; 46(19): 2672-2681
DOI: 10.1055/s-0034-1378900

paper

An Efficient Petasis Boronic–Mannich Reaction of Chiral Lactol Derivatives Prepared from d-Araboascorbic Acid

Hiroki Mandai*

^aDivision of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan Email: mandai@cc.okayama-u.ac.jp Email: suga@cc.okayama-u.ac.jp

,

Hiroshi Yamada

^aDivision of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan Email: mandai@cc.okayama-u.ac.jp Email: suga@cc.okayama-u.ac.jp

,

Keita Shimowaki

^aDivision of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan Email: mandai@cc.okayama-u.ac.jp Email: suga@cc.okayama-u.ac.jp

,

Koichi Mitsudo

^aDivision of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan Email: mandai@cc.okayama-u.ac.jp Email: suga@cc.okayama-u.ac.jp

,

Seiji Suga*

^aDivision of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan Email: mandai@cc.okayama-u.ac.jp Email: suga@cc.okayama-u.ac.jp

^bResearch Center of New Functional Materials for Energy Production, Storage and Transport Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan

^cJapan Science and Technology Agency, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan

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Abstract

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Abstract

Optically active polyhydroxy trans-1,2-amino alcohols were efficiently synthesized in good to excellent yields by the Petasis boronic–Mannich reaction of an amine, an organoboronic acid, and a chiral lactol, which was prepared from d-araboascorbic acid or its diastereomer. Further transformations of the resulting Petasis products were investigated in detail to obtain chiral building blocks containing three continuous stereogenic centers.

Key words

asymmetric synthesis - chiral pool - coupling - diastereoselectivity - domino reaction - lactones

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References

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