Diastereo- and enantioselective intramolecular 1,6-C-H insertion reactions of α-diazo esters catalyzed by chiral dirhodium(II) carboxylates

Motoki Ito; Yuji Kondo; Hisanori Nambu; Masahiro Anada; Koji Takeda; Shunichi Hashimoto

doi:10.1016/j.tetlet.2015.01.125

Diastereo- and enantioselective intramolecular 1,6-C-H insertion reactions of α-diazo esters catalyzed by chiral dirhodium(II) carboxylates

Motoki Ito, Yuji Kondo, Hisanori Nambu, Masahiro Anada, Koji Takeda, Shunichi Hashimoto^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

32 Scopus citations

Abstract

The first catalytic asymmetric intramolecular 1,6-C-H insertion reaction of α-diazo esters is described. With dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh₂(S-PTTL)₄, the C-H insertion proceeded in a chemoselective manner to give 2-alkenyltetrahydropyran-3-carboxylates with up to 95% ee and perfect cis diastereoselectivity.

Original language	English
Pages (from-to)	1397-1400
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.125
State	Published - 2015/03/11

Keywords

Asymmetric catalysis
C-H insertion
Dirhodium(II) complex
Six-membered heterocycle
α-Diazo ester

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2015.01.125

Cite this

@article{2069b091abd74ffea85663e33510c068,

title = "Diastereo- and enantioselective intramolecular 1,6-C-H insertion reactions of α-diazo esters catalyzed by chiral dirhodium(II) carboxylates",

abstract = "The first catalytic asymmetric intramolecular 1,6-C-H insertion reaction of α-diazo esters is described. With dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh2(S-PTTL)4, the C-H insertion proceeded in a chemoselective manner to give 2-alkenyltetrahydropyran-3-carboxylates with up to 95% ee and perfect cis diastereoselectivity.",

keywords = "Asymmetric catalysis, C-H insertion, Dirhodium(II) complex, Six-membered heterocycle, α-Diazo ester",

author = "Motoki Ito and Yuji Kondo and Hisanori Nambu and Masahiro Anada and Koji Takeda and Shunichi Hashimoto",

year = "2015",

month = mar,

day = "11",

doi = "10.1016/j.tetlet.2015.01.125",

language = "英語",

volume = "56",

pages = "1397--1400",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "11",

}

TY - JOUR

T1 - Diastereo- and enantioselective intramolecular 1,6-C-H insertion reactions of α-diazo esters catalyzed by chiral dirhodium(II) carboxylates

AU - Ito, Motoki

AU - Kondo, Yuji

AU - Nambu, Hisanori

AU - Anada, Masahiro

AU - Takeda, Koji

AU - Hashimoto, Shunichi

PY - 2015/3/11

Y1 - 2015/3/11

N2 - The first catalytic asymmetric intramolecular 1,6-C-H insertion reaction of α-diazo esters is described. With dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh2(S-PTTL)4, the C-H insertion proceeded in a chemoselective manner to give 2-alkenyltetrahydropyran-3-carboxylates with up to 95% ee and perfect cis diastereoselectivity.

AB - The first catalytic asymmetric intramolecular 1,6-C-H insertion reaction of α-diazo esters is described. With dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh2(S-PTTL)4, the C-H insertion proceeded in a chemoselective manner to give 2-alkenyltetrahydropyran-3-carboxylates with up to 95% ee and perfect cis diastereoselectivity.

KW - Asymmetric catalysis

KW - C-H insertion

KW - Dirhodium(II) complex

KW - Six-membered heterocycle

KW - α-Diazo ester

UR - http://www.scopus.com/inward/record.url?scp=84923623662&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.01.125

DO - 10.1016/j.tetlet.2015.01.125

M3 - 学術論文

AN - SCOPUS:84923623662

SN - 0040-4039

VL - 56

SP - 1397

EP - 1400

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Diastereo- and enantioselective intramolecular 1,6-C-H insertion reactions of α-diazo esters catalyzed by chiral dirhodium(II) carboxylates

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this