Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels-Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles

Andrés Felipe León Rojas; Ying Yan Chong; Sara Helen Kyne; Bo Xia; Philip Wai Hong Chan

doi:10.1021/acs.orglett.4c00621

Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels-Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles

Andrés Felipe León Rojas
, Ying Yan Chong
, Sara Helen Kyne
, Bo Xia
, Philip Wai Hong Chan

School of Chemistry

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

5 Citations (Scopus)

Abstract

A synthetic method for the enantioselective and regiodivergent synthesis of hexahydro-2H-2,4a-methanonaphthalen-4-yl and octahydro-2,4-methanoazulen-1-yl esters that relies on the gold(I)- and chiral Brønsted acid-catalyzed cycloisomerization/Diels-Alder (CDA) reaction of (E)-1,10-dien-4-yn-3-yl acetates is described.

Original language	English
Pages (from-to)	3037–3042
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.4c00621
Publication status	Published - 19 Apr 2024

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10.1021/acs.orglett.4c00621

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@article{8a51ece8630e44399d3ae7fa2155a6da,

title = "Enantioselective and Regiodivergent Gold and Chiral Br{\o}nsted Acid Catalyzed Cycloisomerization/Diels-Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles",

abstract = "A synthetic method for the enantioselective and regiodivergent synthesis of hexahydro-2H-2,4a-methanonaphthalen-4-yl and octahydro-2,4-methanoazulen-1-yl esters that relies on the gold(I)- and chiral Br{\o}nsted acid-catalyzed cycloisomerization/Diels-Alder (CDA) reaction of (E)-1,10-dien-4-yn-3-yl acetates is described.",

author = "\{Le{\'o}n Rojas\}, \{Andr{\'e}s Felipe\} and Chong, \{Ying Yan\} and Kyne, \{Sara Helen\} and Bo Xia and Chan, \{Philip Wai Hong\}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

month = apr,

day = "19",

doi = "10.1021/acs.orglett.4c00621",

language = "English",

volume = "26",

pages = "3037–3042",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels-Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles. / León Rojas, Andrés Felipe; Chong, Ying Yan; Kyne, Sara Helen et al.
In: Organic Letters, Vol. 26, No. 15, 19.04.2024, p. 3037–3042.

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

TY - JOUR

T1 - Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels-Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates

T2 - Synthesis of Norbornene-Embedded Tricarbocycles

AU - León Rojas, Andrés Felipe

AU - Chong, Ying Yan

AU - Kyne, Sara Helen

AU - Xia, Bo

AU - Chan, Philip Wai Hong

PY - 2024/4/19

Y1 - 2024/4/19

N2 - A synthetic method for the enantioselective and regiodivergent synthesis of hexahydro-2H-2,4a-methanonaphthalen-4-yl and octahydro-2,4-methanoazulen-1-yl esters that relies on the gold(I)- and chiral Brønsted acid-catalyzed cycloisomerization/Diels-Alder (CDA) reaction of (E)-1,10-dien-4-yn-3-yl acetates is described.

AB - A synthetic method for the enantioselective and regiodivergent synthesis of hexahydro-2H-2,4a-methanonaphthalen-4-yl and octahydro-2,4-methanoazulen-1-yl esters that relies on the gold(I)- and chiral Brønsted acid-catalyzed cycloisomerization/Diels-Alder (CDA) reaction of (E)-1,10-dien-4-yn-3-yl acetates is described.

UR - https://www.scopus.com/pages/publications/85189506613

U2 - 10.1021/acs.orglett.4c00621

DO - 10.1021/acs.orglett.4c00621

M3 - Article

AN - SCOPUS:85189506613

SN - 1523-7060

VL - 26

SP - 3037

EP - 3042

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels-Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles

Abstract

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