Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes: synthesis of a fragment of (+)-vibsanin A

Akihiro Sakama; Yoshiyasu Nishimura; Yuko Motohashi; Keisuke Yoshida; Ken ichi Takao

doi:10.1016/j.tet.2016.07.030

Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes: synthesis of a fragment of (+)-vibsanin A

Akihiro Sakama, Yoshiyasu Nishimura, Yuko Motohashi, Keisuke Yoshida, Ken ichi Takao

Department of Applied Chemistry

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

3 Citations (Scopus)

Abstract

Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes is described. Sugar-derived aldehydes were allylated with geranylboronate or nerylboronate to provide γ-adducts possessing quaternary stereocenters with high diastereoselectivity. The reaction was applied to the synthesis of a fragment of (+)-vibsanin A.

Original language	English
Pages (from-to)	5465-5471
Number of pages	7
Journal	Tetrahedron
Volume	72
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2016.07.030
Publication status	Published - 2016

Keywords

Allylation
Boronates
Carbohydrates
Diastereoselectivity
Quaternary stereocenter

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2016.07.030

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title = "Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes: synthesis of a fragment of (+)-vibsanin A",

abstract = "Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes is described. Sugar-derived aldehydes were allylated with geranylboronate or nerylboronate to provide γ-adducts possessing quaternary stereocenters with high diastereoselectivity. The reaction was applied to the synthesis of a fragment of (+)-vibsanin A.",

keywords = "Allylation, Boronates, Carbohydrates, Diastereoselectivity, Quaternary stereocenter",

author = "Akihiro Sakama and Yoshiyasu Nishimura and Yuko Motohashi and Keisuke Yoshida and Takao, {Ken ichi}",

note = "Funding Information: This work was supported in part by the Ministry of Education, Culture, Sports, Science, and Technology -Supported Program for the Strategic Research Foundation at Private Universities, 2012–2016, and the Keio University Doctorate Student Grant-in-Aid Program. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

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doi = "10.1016/j.tet.2016.07.030",

language = "English",

volume = "72",

pages = "5465--5471",

journal = "Tetrahedron",

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TY - JOUR

T1 - Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes

T2 - synthesis of a fragment of (+)-vibsanin A

AU - Sakama, Akihiro

AU - Nishimura, Yoshiyasu

AU - Motohashi, Yuko

AU - Yoshida, Keisuke

AU - Takao, Ken ichi

N1 - Funding Information: This work was supported in part by the Ministry of Education, Culture, Sports, Science, and Technology -Supported Program for the Strategic Research Foundation at Private Universities, 2012–2016, and the Keio University Doctorate Student Grant-in-Aid Program. Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes is described. Sugar-derived aldehydes were allylated with geranylboronate or nerylboronate to provide γ-adducts possessing quaternary stereocenters with high diastereoselectivity. The reaction was applied to the synthesis of a fragment of (+)-vibsanin A.

AB - Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes is described. Sugar-derived aldehydes were allylated with geranylboronate or nerylboronate to provide γ-adducts possessing quaternary stereocenters with high diastereoselectivity. The reaction was applied to the synthesis of a fragment of (+)-vibsanin A.

KW - Allylation

KW - Boronates

KW - Carbohydrates

KW - Diastereoselectivity

KW - Quaternary stereocenter

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DO - 10.1016/j.tet.2016.07.030

M3 - Article

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SN - 0040-4020

VL - 72

SP - 5465

EP - 5471

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes: synthesis of a fragment of (+)-vibsanin A

Abstract

Keywords

ASJC Scopus subject areas

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