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

Harvard University

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

158 Scopus citations

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
State	Published - 18 Jun 1993
Externally published	Yes

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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",

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T1 - Catalytic enantioselective diels-alder addition to furan provides a direct synthetic route to many chiral natural products

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.

UR - http://www.scopus.com/inward/record.url?scp=0027160174&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)60594-4

DO - 10.1016/S0040-4039(00)60594-4

M3 - 文章

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SN - 0040-4039

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SP - 3979

EP - 3982

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

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

Abstract

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