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

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

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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.

Original language	English
Article number	ss-2014-c0373-op
Pages (from-to)	2672-2681
Number of pages	10
Journal	Synthesis (Germany)
Volume	46
Issue number	19
DOIs	https://doi.org/10.1055/s-0034-1378900
Publication status	Published - Oct 1 2014

Keywords

asymmetric synthesis
chiral pool
coupling
diastereoselectivity
domino reaction
lactones

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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AU - Mandai, Hiroki

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AU - Shimowaki, Keita

AU - Mitsudo, Koichi

AU - Suga, Seiji

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

PY - 2014/10/1

Y1 - 2014/10/1

N2 - 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.

AB - 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.

KW - asymmetric synthesis

KW - chiral pool

KW - coupling

KW - diastereoselectivity

KW - domino reaction

KW - lactones

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

Abstract

Keywords

ASJC Scopus subject areas

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