Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst: Structural tuning of salen ligand

Biswajit Saha; Tatsuya Uchida; Tsutomu Katsuki

doi:10.1016/S0957-4166(03)00167-8

Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst: Structural tuning of salen ligand

Biswajit Saha, Tatsuya Uchida, Tsutomu Katsuki

Division for Experimental Natural Science

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

46 Citations (Scopus)

Abstract

Intramolecular cyclopropanation of alkenyl α-diazoacetates and alkenyl diazomethyl ketones was examined by using optically active (ON⁺)Ru(II)(salen) and Co(II)(salen) complexes as catalysts. For the cyclization of 2-alkenyl α-diazoacetates, Co(II)(salen) complexes 9 and 10 were found to be superior catalysts to the corresponding (ON⁺)Ru(II)(salen) complexes 4 and 5. On the other hand, (ON⁺)Ru(II)(salen) complex 2 was found to be the catalyst of choice for the cyclization of 3-alkenyl diazomethyl ketones, and complex 4 was found to be a good catalyst for the cyclization of (E)-4-alkenyl diazomethyl ketones. The present study demonstrates that metallosalen complexes, especially optically active (ON⁺)Ru(II)(salen) and Co(II)(salen) complexes, can serve as efficient catalysts for the cyclization of alkenyl diazocarbonyl compounds, if a suitable salen ligand is used as the chiral auxiliary.

Original language	English
Pages (from-to)	823-836
Number of pages	14
Journal	Tetrahedron Asymmetry
Volume	14
Issue number	7
DOIs	https://doi.org/10.1016/S0957-4166(03)00167-8
Publication status	Published - Apr 4 2003

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst: Structural tuning of salen ligand",

abstract = "Intramolecular cyclopropanation of alkenyl α-diazoacetates and alkenyl diazomethyl ketones was examined by using optically active (ON+)Ru(II)(salen) and Co(II)(salen) complexes as catalysts. For the cyclization of 2-alkenyl α-diazoacetates, Co(II)(salen) complexes 9 and 10 were found to be superior catalysts to the corresponding (ON+)Ru(II)(salen) complexes 4 and 5. On the other hand, (ON+)Ru(II)(salen) complex 2 was found to be the catalyst of choice for the cyclization of 3-alkenyl diazomethyl ketones, and complex 4 was found to be a good catalyst for the cyclization of (E)-4-alkenyl diazomethyl ketones. The present study demonstrates that metallosalen complexes, especially optically active (ON+)Ru(II)(salen) and Co(II)(salen) complexes, can serve as efficient catalysts for the cyclization of alkenyl diazocarbonyl compounds, if a suitable salen ligand is used as the chiral auxiliary.",

author = "Biswajit Saha and Tatsuya Uchida and Tsutomu Katsuki",

year = "2003",

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doi = "10.1016/S0957-4166(03)00167-8",

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TY - JOUR

T1 - Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst

T2 - Structural tuning of salen ligand

AU - Saha, Biswajit

AU - Uchida, Tatsuya

AU - Katsuki, Tsutomu

PY - 2003/4/4

Y1 - 2003/4/4

N2 - Intramolecular cyclopropanation of alkenyl α-diazoacetates and alkenyl diazomethyl ketones was examined by using optically active (ON+)Ru(II)(salen) and Co(II)(salen) complexes as catalysts. For the cyclization of 2-alkenyl α-diazoacetates, Co(II)(salen) complexes 9 and 10 were found to be superior catalysts to the corresponding (ON+)Ru(II)(salen) complexes 4 and 5. On the other hand, (ON+)Ru(II)(salen) complex 2 was found to be the catalyst of choice for the cyclization of 3-alkenyl diazomethyl ketones, and complex 4 was found to be a good catalyst for the cyclization of (E)-4-alkenyl diazomethyl ketones. The present study demonstrates that metallosalen complexes, especially optically active (ON+)Ru(II)(salen) and Co(II)(salen) complexes, can serve as efficient catalysts for the cyclization of alkenyl diazocarbonyl compounds, if a suitable salen ligand is used as the chiral auxiliary.

AB - Intramolecular cyclopropanation of alkenyl α-diazoacetates and alkenyl diazomethyl ketones was examined by using optically active (ON+)Ru(II)(salen) and Co(II)(salen) complexes as catalysts. For the cyclization of 2-alkenyl α-diazoacetates, Co(II)(salen) complexes 9 and 10 were found to be superior catalysts to the corresponding (ON+)Ru(II)(salen) complexes 4 and 5. On the other hand, (ON+)Ru(II)(salen) complex 2 was found to be the catalyst of choice for the cyclization of 3-alkenyl diazomethyl ketones, and complex 4 was found to be a good catalyst for the cyclization of (E)-4-alkenyl diazomethyl ketones. The present study demonstrates that metallosalen complexes, especially optically active (ON+)Ru(II)(salen) and Co(II)(salen) complexes, can serve as efficient catalysts for the cyclization of alkenyl diazocarbonyl compounds, if a suitable salen ligand is used as the chiral auxiliary.

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M3 - Article

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SN - 0957-4166

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 7

ER -

Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst: Structural tuning of salen ligand

Abstract

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