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

応用化学科

研究成果: Article › 査読

19 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	481-484
ページ数	4
ジャーナル	Synlett
号	4
DOI	https://doi.org/10.1055/s-2001-12333
出版ステータス	Published - 2001

ASJC Scopus subject areas

有機化学

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10.1055/s-2001-12333

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title = "Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates",

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",

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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

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SP - 481

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JO - Synlett

JF - Synlett

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ER -

Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates

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