Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates

T. Nagatsuka; S. Yamaguchi; K. Totani; K. I. Takao; K. I. Tadano

doi:10.1055/s-2001-12333

Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates

T. Nagatsuka
, S. Yamaguchi
, K. Totani
, K. I. Takao
, K. I. Tadano

Department of Applied Chemistry

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

19 Citations (Scopus)

Abstract

The Diels-Alder reactions of some carbohydrate derivatives, as chiral acrylic esters, with cyclopentadiene proceed highly diastereoselectively to provide the adducts carrying a norbornene carboxylate. By reductive removal of the carbohydrate templates from the adducts, both 2S and 2R-enriched 5-norbornene-2-methanol are obtained.

Original language	English
Pages (from-to)	481-484
Number of pages	4
Journal	Synlett
Issue number	4
DOIs	https://doi.org/10.1055/s-2001-12333
Publication status	Published - 2001

Keywords

Asymmetric synthesis
Cyclopentadiene
Diastereoselectivity
Diels-Alder reaction
Norbornene derivatives

ASJC Scopus subject areas

Organic Chemistry

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abstract = "The Diels-Alder reactions of some carbohydrate derivatives, as chiral acrylic esters, with cyclopentadiene proceed highly diastereoselectively to provide the adducts carrying a norbornene carboxylate. By reductive removal of the carbohydrate templates from the adducts, both 2S and 2R-enriched 5-norbornene-2-methanol are obtained.",

keywords = "Asymmetric synthesis, Cyclopentadiene, Diastereoselectivity, Diels-Alder reaction, Norbornene derivatives",

author = "T. Nagatsuka and S. Yamaguchi and K. Totani and Takao, \{K. I.\} and Tadano, \{K. I.\}",

year = "2001",

doi = "10.1055/s-2001-12333",

language = "English",

pages = "481--484",

journal = "Synlett",

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T1 - Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates

AU - Nagatsuka, T.

AU - Yamaguchi, S.

AU - Totani, K.

AU - Takao, K. I.

AU - Tadano, K. I.

PY - 2001

Y1 - 2001

N2 - The Diels-Alder reactions of some carbohydrate derivatives, as chiral acrylic esters, with cyclopentadiene proceed highly diastereoselectively to provide the adducts carrying a norbornene carboxylate. By reductive removal of the carbohydrate templates from the adducts, both 2S and 2R-enriched 5-norbornene-2-methanol are obtained.

AB - The Diels-Alder reactions of some carbohydrate derivatives, as chiral acrylic esters, with cyclopentadiene proceed highly diastereoselectively to provide the adducts carrying a norbornene carboxylate. By reductive removal of the carbohydrate templates from the adducts, both 2S and 2R-enriched 5-norbornene-2-methanol are obtained.

KW - Asymmetric synthesis

KW - Cyclopentadiene

KW - Diastereoselectivity

KW - Diels-Alder reaction

KW - Norbornene derivatives

UR - https://www.scopus.com/pages/publications/0035075035

UR - https://www.scopus.com/pages/publications/0035075035#tab=citedBy

U2 - 10.1055/s-2001-12333

DO - 10.1055/s-2001-12333

M3 - Article

AN - SCOPUS:0035075035

SN - 0936-5214

SP - 481

EP - 484

JO - Synlett

JF - Synlett

IS - 4

ER -

Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates

Abstract

Keywords

ASJC Scopus subject areas

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