Catalytic enantioselective diels-alder addition to furan provides a direct synthetic route to many chiral natural products

E. J. Corey; Teck Peng Loh

doi:10.1016/S0040-4039(00)60594-4

Catalytic enantioselective diels-alder addition to furan provides a direct synthetic route to many chiral natural products

E. J. Corey^*, Teck Peng Loh

^*Corresponding author for this work

Harvard University

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

158 Citations (Scopus)

Abstract

An oxazaborolidine derived from N-tosyl (αS,βR)-β-methyltryptophan (1)catalyzes the Diels-Alder reaction of 2-bromoacrolein and furan with 96:4 enantioselectivity, leading to an efficient synthesis of numerous chiral 7-oxabicyclo[2.2.1]heptene derivatives.

Original language	English
Pages (from-to)	3979-3982
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4039(00)60594-4
Publication status	Published - Jun 18 1993
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Catalytic enantioselective diels-alder addition to furan provides a direct synthetic route to many chiral natural products",

abstract = "An oxazaborolidine derived from N-tosyl (αS,βR)-β-methyltryptophan (1)catalyzes the Diels-Alder reaction of 2-bromoacrolein and furan with 96:4 enantioselectivity, leading to an efficient synthesis of numerous chiral 7-oxabicyclo[2.2.1]heptene derivatives.",

author = "Corey, \{E. J.\} and Loh, \{Teck Peng\}",

year = "1993",

month = jun,

day = "18",

doi = "10.1016/S0040-4039(00)60594-4",

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journal = "Tetrahedron Letters",

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AU - Corey, E. J.

AU - Loh, Teck Peng

PY - 1993/6/18

Y1 - 1993/6/18

N2 - An oxazaborolidine derived from N-tosyl (αS,βR)-β-methyltryptophan (1)catalyzes the Diels-Alder reaction of 2-bromoacrolein and furan with 96:4 enantioselectivity, leading to an efficient synthesis of numerous chiral 7-oxabicyclo[2.2.1]heptene derivatives.

AB - An oxazaborolidine derived from N-tosyl (αS,βR)-β-methyltryptophan (1)catalyzes the Diels-Alder reaction of 2-bromoacrolein and furan with 96:4 enantioselectivity, leading to an efficient synthesis of numerous chiral 7-oxabicyclo[2.2.1]heptene derivatives.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Catalytic enantioselective diels-alder addition to furan provides a direct synthetic route to many chiral natural products

Abstract

ASJC Scopus Subject Areas

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