Electrophilic cyclization of 2-(2',3'-allenyl)acetylacetates with iodine using calcium hydride as the base

Baoqiang Wan; Xuefeng Jiang; Guochen Jia; Shengming Ma

doi:10.1002/ejoc.201200527

Electrophilic cyclization of 2-(2',3'-allenyl)acetylacetates with iodine using calcium hydride as the base

Baoqiang Wan
, Xuefeng Jiang
, Guochen Jia
, Shengming Ma^*

^*Corresponding author for this work

CAS - Shanghai Institute of Organic Chemistry
Hong Kong University of Science and Technology
East China Normal University

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

13 Scopus citations

Abstract

A facile and efficient protocol for the synthesis of 4,5-dihydrofuran derivatives via iodine-mediated cyclization of various 2-(2',3'-allenyl) acetylacetates with CaH ₂ as the base has been developed. The yields range from moderate to good. The resulting products can be used for further elaboration by palladium-catalyzed coupling reactions. A facile and efficient protocol for the synthesis of 4,5-dihydrofuran derivatives via iodine-mediated cyclization of various 2-(2',3'-allenyl)acetylacetates with CaH ₂ as the base has been developed. The yields range from moderate to good. The resulting products can be used for further elaboration by palladium-catalyzed coupling reactions.

Original language	English
Pages (from-to)	4373-4379
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	23
DOIs	https://doi.org/10.1002/ejoc.201200527
State	Published - Aug 2012
Externally published	Yes

Keywords

Allenes
Cyclization
Iodine
Oxygen heterocycles

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10.1002/ejoc.201200527

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title = "Electrophilic cyclization of 2-(2',3'-allenyl)acetylacetates with iodine using calcium hydride as the base",

abstract = "A facile and efficient protocol for the synthesis of 4,5-dihydrofuran derivatives via iodine-mediated cyclization of various 2-(2',3'-allenyl) acetylacetates with CaH 2 as the base has been developed. The yields range from moderate to good. The resulting products can be used for further elaboration by palladium-catalyzed coupling reactions. A facile and efficient protocol for the synthesis of 4,5-dihydrofuran derivatives via iodine-mediated cyclization of various 2-(2',3'-allenyl)acetylacetates with CaH 2 as the base has been developed. The yields range from moderate to good. The resulting products can be used for further elaboration by palladium-catalyzed coupling reactions.",

keywords = "Allenes, Cyclization, Iodine, Oxygen heterocycles",

author = "Baoqiang Wan and Xuefeng Jiang and Guochen Jia and Shengming Ma",

year = "2012",

month = aug,

doi = "10.1002/ejoc.201200527",

language = "英语",

pages = "4373--4379",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "23",

}

TY - JOUR

T1 - Electrophilic cyclization of 2-(2',3'-allenyl)acetylacetates with iodine using calcium hydride as the base

AU - Wan, Baoqiang

AU - Jiang, Xuefeng

AU - Jia, Guochen

AU - Ma, Shengming

PY - 2012/8

Y1 - 2012/8

N2 - A facile and efficient protocol for the synthesis of 4,5-dihydrofuran derivatives via iodine-mediated cyclization of various 2-(2',3'-allenyl) acetylacetates with CaH 2 as the base has been developed. The yields range from moderate to good. The resulting products can be used for further elaboration by palladium-catalyzed coupling reactions. A facile and efficient protocol for the synthesis of 4,5-dihydrofuran derivatives via iodine-mediated cyclization of various 2-(2',3'-allenyl)acetylacetates with CaH 2 as the base has been developed. The yields range from moderate to good. The resulting products can be used for further elaboration by palladium-catalyzed coupling reactions.

AB - A facile and efficient protocol for the synthesis of 4,5-dihydrofuran derivatives via iodine-mediated cyclization of various 2-(2',3'-allenyl) acetylacetates with CaH 2 as the base has been developed. The yields range from moderate to good. The resulting products can be used for further elaboration by palladium-catalyzed coupling reactions. A facile and efficient protocol for the synthesis of 4,5-dihydrofuran derivatives via iodine-mediated cyclization of various 2-(2',3'-allenyl)acetylacetates with CaH 2 as the base has been developed. The yields range from moderate to good. The resulting products can be used for further elaboration by palladium-catalyzed coupling reactions.

KW - Allenes

KW - Cyclization

KW - Iodine

KW - Oxygen heterocycles

UR - https://www.scopus.com/pages/publications/84864750932

U2 - 10.1002/ejoc.201200527

DO - 10.1002/ejoc.201200527

M3 - 文章

AN - SCOPUS:84864750932

SN - 1434-193X

SP - 4373

EP - 4379

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 23

ER -

Electrophilic cyclization of 2-(2',3'-allenyl)acetylacetates with iodine using calcium hydride as the base

Abstract

Keywords

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