Catalytic enantioselective intermolecular cycloaddition of diazodiketoester-derived carbonyl ylides with indoles using chiral dirhodium(II) carboxylates

Naoyuki Shimada; Tadashi Oohara; Janagiraman Krishnamurthi; Hisanori Nambu; Shunichi Hashimoto

doi:10.1021/ol2027625

Catalytic enantioselective intermolecular cycloaddition of diazodiketoester-derived carbonyl ylides with indoles using chiral dirhodium(II) carboxylates

Naoyuki Shimada, Tadashi Oohara, Janagiraman Krishnamurthi, Hisanori Nambu, Shunichi Hashimoto^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

75 Scopus citations

Abstract

The first example of enantioselective intermolecular cycloaddition of carbonyl ylides with indoles is described. The cycloaddition of five- and six-membered carbonyl ylides derived from diazodiketoesters with N-methylindoles under catalysis by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert- leucinate], Rh ₂(S-TCPTTL) ₄, gave cycloadducts in high yields and with high levels of enantioselectivity (up to 99% ee) as well as excellent exo diastereoselectivity.

Original language	English
Pages (from-to)	6284-6287
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	23
DOIs	https://doi.org/10.1021/ol2027625
State	Published - 2011/12/02

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Catalytic enantioselective intermolecular cycloaddition of diazodiketoester-derived carbonyl ylides with indoles using chiral dirhodium(II) carboxylates",

abstract = "The first example of enantioselective intermolecular cycloaddition of carbonyl ylides with indoles is described. The cycloaddition of five- and six-membered carbonyl ylides derived from diazodiketoesters with N-methylindoles under catalysis by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert- leucinate], Rh 2(S-TCPTTL) 4, gave cycloadducts in high yields and with high levels of enantioselectivity (up to 99% ee) as well as excellent exo diastereoselectivity.",

author = "Naoyuki Shimada and Tadashi Oohara and Janagiraman Krishnamurthi and Hisanori Nambu and Shunichi Hashimoto",

year = "2011",

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doi = "10.1021/ol2027625",

language = "英語",

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T1 - Catalytic enantioselective intermolecular cycloaddition of diazodiketoester-derived carbonyl ylides with indoles using chiral dirhodium(II) carboxylates

AU - Shimada, Naoyuki

AU - Oohara, Tadashi

AU - Krishnamurthi, Janagiraman

AU - Nambu, Hisanori

AU - Hashimoto, Shunichi

PY - 2011/12/2

Y1 - 2011/12/2

N2 - The first example of enantioselective intermolecular cycloaddition of carbonyl ylides with indoles is described. The cycloaddition of five- and six-membered carbonyl ylides derived from diazodiketoesters with N-methylindoles under catalysis by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert- leucinate], Rh 2(S-TCPTTL) 4, gave cycloadducts in high yields and with high levels of enantioselectivity (up to 99% ee) as well as excellent exo diastereoselectivity.

AB - The first example of enantioselective intermolecular cycloaddition of carbonyl ylides with indoles is described. The cycloaddition of five- and six-membered carbonyl ylides derived from diazodiketoesters with N-methylindoles under catalysis by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert- leucinate], Rh 2(S-TCPTTL) 4, gave cycloadducts in high yields and with high levels of enantioselectivity (up to 99% ee) as well as excellent exo diastereoselectivity.

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U2 - 10.1021/ol2027625

DO - 10.1021/ol2027625

M3 - 学術論文

C2 - 22047068

AN - SCOPUS:82355160842

SN - 1523-7060

VL - 13

SP - 6284

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JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Catalytic enantioselective intermolecular cycloaddition of diazodiketoester-derived carbonyl ylides with indoles using chiral dirhodium(II) carboxylates

Abstract

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