Catalytic asymmetric synthesis of the endo -6-Aryl-8-oxabicyclo[3.2.1]oct- 3-en-2-one natural product from ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh2(S -TCPTTL)4

Naoyuki Shimada; Taiki Hanari; Yasunobu Kurosaki; Koji Takeda; Masahiro Anada; Hisanori Nambu; Motoo Shiro; Shunichi Hashimoto

doi:10.1021/jo101175b

Catalytic asymmetric synthesis of the endo -6-Aryl-8-oxabicyclo[3.2.1]oct- 3-en-2-one natural product from ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh₂(S -TCPTTL)₄

Naoyuki Shimada, Taiki Hanari, Yasunobu Kurosaki, Koji Takeda, Masahiro Anada, Hisanori Nambu, Motoo Shiro, Shunichi Hashimoto^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

48 Scopus citations

Abstract

The reaction of a six-membered cyclic formyl-carbonyl ylide derived from α-diazo-β-ketoester with phenylacetylene derivatives under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh₂(S-TCPTTL)₄, provides cycloadducts containing an 8-oxabicyclo[3.2.1]octane ring system in up to 97% ee. This represents the first example of an enantioselective 1,3-dipolar cycloaddition of a cyclic formyl-carbonyl ylide. Using this catalytic process, an asymmetric synthesis of endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product 1 from Ligusticum chuanxing Hort. has been achieved.

Original language	English
Pages (from-to)	6039-6042
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	75
Issue number	17
DOIs	https://doi.org/10.1021/jo101175b
State	Published - 2010/09/03

ASJC Scopus subject areas

Organic Chemistry

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Shimada, N., Hanari, T., Kurosaki, Y., Takeda, K., Anada, M., Nambu, H., Shiro, M., & Hashimoto, S. (2010). Catalytic asymmetric synthesis of the endo -6-Aryl-8-oxabicyclo[3.2.1]oct- 3-en-2-one natural product from ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh₂(S -TCPTTL)₄. Journal of Organic Chemistry, 75(17), 6039-6042. https://doi.org/10.1021/jo101175b

@article{9909077363244abb9c8d21e13500b1ba,

title = "Catalytic asymmetric synthesis of the endo -6-Aryl-8-oxabicyclo[3.2.1]oct- 3-en-2-one natural product from ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh2(S -TCPTTL)4",

abstract = "The reaction of a six-membered cyclic formyl-carbonyl ylide derived from α-diazo-β-ketoester with phenylacetylene derivatives under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, provides cycloadducts containing an 8-oxabicyclo[3.2.1]octane ring system in up to 97% ee. This represents the first example of an enantioselective 1,3-dipolar cycloaddition of a cyclic formyl-carbonyl ylide. Using this catalytic process, an asymmetric synthesis of endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product 1 from Ligusticum chuanxing Hort. has been achieved.",

author = "Naoyuki Shimada and Taiki Hanari and Yasunobu Kurosaki and Koji Takeda and Masahiro Anada and Hisanori Nambu and Motoo Shiro and Shunichi Hashimoto",

year = "2010",

month = sep,

day = "3",

doi = "10.1021/jo101175b",

language = "英語",

volume = "75",

pages = "6039--6042",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

Shimada, N, Hanari, T, Kurosaki, Y, Takeda, K, Anada, M, Nambu, H, Shiro, M & Hashimoto, S 2010, 'Catalytic asymmetric synthesis of the endo -6-Aryl-8-oxabicyclo[3.2.1]oct- 3-en-2-one natural product from ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh₂(S -TCPTTL)₄', Journal of Organic Chemistry, vol. 75, no. 17, pp. 6039-6042. https://doi.org/10.1021/jo101175b

Catalytic asymmetric synthesis of the endo -6-Aryl-8-oxabicyclo[3.2.1]oct- 3-en-2-one natural product from ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh₂(S -TCPTTL)₄. / Shimada, Naoyuki; Hanari, Taiki; Kurosaki, Yasunobu et al.
In: Journal of Organic Chemistry, Vol. 75, No. 17, 03.09.2010, p. 6039-6042.

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

TY - JOUR

T1 - Catalytic asymmetric synthesis of the endo -6-Aryl-8-oxabicyclo[3.2.1]oct- 3-en-2-one natural product from ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh2(S -TCPTTL)4

AU - Shimada, Naoyuki

AU - Hanari, Taiki

AU - Kurosaki, Yasunobu

AU - Takeda, Koji

AU - Anada, Masahiro

AU - Nambu, Hisanori

AU - Shiro, Motoo

AU - Hashimoto, Shunichi

PY - 2010/9/3

Y1 - 2010/9/3

N2 - The reaction of a six-membered cyclic formyl-carbonyl ylide derived from α-diazo-β-ketoester with phenylacetylene derivatives under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, provides cycloadducts containing an 8-oxabicyclo[3.2.1]octane ring system in up to 97% ee. This represents the first example of an enantioselective 1,3-dipolar cycloaddition of a cyclic formyl-carbonyl ylide. Using this catalytic process, an asymmetric synthesis of endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product 1 from Ligusticum chuanxing Hort. has been achieved.

AB - The reaction of a six-membered cyclic formyl-carbonyl ylide derived from α-diazo-β-ketoester with phenylacetylene derivatives under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, provides cycloadducts containing an 8-oxabicyclo[3.2.1]octane ring system in up to 97% ee. This represents the first example of an enantioselective 1,3-dipolar cycloaddition of a cyclic formyl-carbonyl ylide. Using this catalytic process, an asymmetric synthesis of endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product 1 from Ligusticum chuanxing Hort. has been achieved.

UR - http://www.scopus.com/inward/record.url?scp=77956133889&partnerID=8YFLogxK

U2 - 10.1021/jo101175b

DO - 10.1021/jo101175b

M3 - 学術論文

C2 - 20698712

AN - SCOPUS:77956133889

SN - 0022-3263

VL - 75

SP - 6039

EP - 6042

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -