Enantioselective photocyclization of acrylanilides and N-Ethyl-N-methylbenzoylformamide in inclusion crystals with (R,R)-(-)-[trans]-2,3-bis(α-hydroxydiphenylmethyl)-1,4-dioxaspiro-[4.4]nonan e and -[4.5]decane. Mechanistic study based on x-ray crystal structure analyses

Shigeru Ohba, Hiroyuki Hosomi, Koichi Tanaka, Hisakazu Miyamoto, Fumio Toda

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Abstract

X-Ray structure analyses of the inclusion complexes indicated that the high stereo- and enantioselectivities in photocyclization of cyclohex-1-enecarboic acid methyl-phenyl-amide (3), N-methyl, N-{(E)-methylmethacryloyl}anilide (5), N-methyl, N-(methacryloyl)anilide (8), and N-ethyl-N-methylbenzoylformamide (10) are the result of their chiral conformations in the clathrate crystalline environment with the title chiral hosts [(-)-1 and (-)-2, respectively]. The chirality of acrylanilides and benzoylformamide can be indicated by the sign of the torsion angle in the backbone of the molecule, C-N-C(=O)-C and O=C(-Ph)-C(=O)-N, respectively. A partial single-crystal-to-single-crystal transformation of 1:1 complex of 10 with (-)-1 was performed by photoirradiation to observe in situ the photoproduct.

Original languageEnglish
Pages (from-to)2075-2085
Number of pages11
JournalBulletin of the Chemical Society of Japan
Volume73
Issue number9
DOIs
Publication statusPublished - 2000 Sep

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Anilides
Crystal structure
Single crystals
Stereoselectivity
X rays
Crystals
Chirality
Enantioselectivity
Amides
Torsional stress
Conformations
Crystalline materials
Molecules
Acids
decane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Enantioselective photocyclization of acrylanilides and N-Ethyl-N-methylbenzoylformamide in inclusion crystals with (R,R)-(-)-[trans]-2,3-bis(α-hydroxydiphenylmethyl)-1,4-dioxaspiro-[4.4]nonan e and -[4.5]decane. Mechanistic study based on x-ray crystal structure analyses",
abstract = "X-Ray structure analyses of the inclusion complexes indicated that the high stereo- and enantioselectivities in photocyclization of cyclohex-1-enecarboic acid methyl-phenyl-amide (3), N-methyl, N-{(E)-methylmethacryloyl}anilide (5), N-methyl, N-(methacryloyl)anilide (8), and N-ethyl-N-methylbenzoylformamide (10) are the result of their chiral conformations in the clathrate crystalline environment with the title chiral hosts [(-)-1 and (-)-2, respectively]. The chirality of acrylanilides and benzoylformamide can be indicated by the sign of the torsion angle in the backbone of the molecule, C-N-C(=O)-C and O=C(-Ph)-C(=O)-N, respectively. A partial single-crystal-to-single-crystal transformation of 1:1 complex of 10 with (-)-1 was performed by photoirradiation to observe in situ the photoproduct.",
author = "Shigeru Ohba and Hiroyuki Hosomi and Koichi Tanaka and Hisakazu Miyamoto and Fumio Toda",
year = "2000",
month = "9",
doi = "10.1246/bcsj.73.2075",
language = "English",
volume = "73",
pages = "2075--2085",
journal = "Bulletin of the Chemical Society of Japan",
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TY - JOUR

T1 - Enantioselective photocyclization of acrylanilides and N-Ethyl-N-methylbenzoylformamide in inclusion crystals with (R,R)-(-)-[trans]-2,3-bis(α-hydroxydiphenylmethyl)-1,4-dioxaspiro-[4.4]nonan e and -[4.5]decane. Mechanistic study based on x-ray crystal structure analyses

AU - Ohba, Shigeru

AU - Hosomi, Hiroyuki

AU - Tanaka, Koichi

AU - Miyamoto, Hisakazu

AU - Toda, Fumio

PY - 2000/9

Y1 - 2000/9

N2 - X-Ray structure analyses of the inclusion complexes indicated that the high stereo- and enantioselectivities in photocyclization of cyclohex-1-enecarboic acid methyl-phenyl-amide (3), N-methyl, N-{(E)-methylmethacryloyl}anilide (5), N-methyl, N-(methacryloyl)anilide (8), and N-ethyl-N-methylbenzoylformamide (10) are the result of their chiral conformations in the clathrate crystalline environment with the title chiral hosts [(-)-1 and (-)-2, respectively]. The chirality of acrylanilides and benzoylformamide can be indicated by the sign of the torsion angle in the backbone of the molecule, C-N-C(=O)-C and O=C(-Ph)-C(=O)-N, respectively. A partial single-crystal-to-single-crystal transformation of 1:1 complex of 10 with (-)-1 was performed by photoirradiation to observe in situ the photoproduct.

AB - X-Ray structure analyses of the inclusion complexes indicated that the high stereo- and enantioselectivities in photocyclization of cyclohex-1-enecarboic acid methyl-phenyl-amide (3), N-methyl, N-{(E)-methylmethacryloyl}anilide (5), N-methyl, N-(methacryloyl)anilide (8), and N-ethyl-N-methylbenzoylformamide (10) are the result of their chiral conformations in the clathrate crystalline environment with the title chiral hosts [(-)-1 and (-)-2, respectively]. The chirality of acrylanilides and benzoylformamide can be indicated by the sign of the torsion angle in the backbone of the molecule, C-N-C(=O)-C and O=C(-Ph)-C(=O)-N, respectively. A partial single-crystal-to-single-crystal transformation of 1:1 complex of 10 with (-)-1 was performed by photoirradiation to observe in situ the photoproduct.

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