Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization

Noriaki Itagaki; Mari Kimura; Tsutomu Sugahara; Yoshiharu Iwabuchi

doi:10.1021/ol051569d

Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization

Noriaki Itagaki, Mari Kimura, Tsutomu Sugahara, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

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

90 Citations (Scopus)

Abstract

(Chemical Equation Presented) The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and encto-7-hydroxybicyclo[3.2.1]octan- 2-one, featuring an α-amino acid catalyzed intramolecular aldolization of σ-symmetric substrates, are described. A high enantioselectivity and a high catalytic efficiency have been exhibited by (4R,2S)-tetrabutylammonium 4-TBDPSoxy-prolinate in the aldolization of 3-(4-oxocyclohexyl)propionaldehyde to give highly enantiomerically enriched (1S,5R,8R)-8-hydroxybicyclo[3.3.1] nonan-2-one.

Original language	English
Pages (from-to)	4185-4188
Number of pages	4
Journal	Organic letters
Volume	7
Issue number	19
DOIs	https://doi.org/10.1021/ol051569d
Publication status	Published - 2005 Sep 15

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol051569d

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title = "Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization",

abstract = "(Chemical Equation Presented) The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and encto-7-hydroxybicyclo[3.2.1]octan- 2-one, featuring an α-amino acid catalyzed intramolecular aldolization of σ-symmetric substrates, are described. A high enantioselectivity and a high catalytic efficiency have been exhibited by (4R,2S)-tetrabutylammonium 4-TBDPSoxy-prolinate in the aldolization of 3-(4-oxocyclohexyl)propionaldehyde to give highly enantiomerically enriched (1S,5R,8R)-8-hydroxybicyclo[3.3.1] nonan-2-one.",

author = "Noriaki Itagaki and Mari Kimura and Tsutomu Sugahara and Yoshiharu Iwabuchi",

year = "2005",

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doi = "10.1021/ol051569d",

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T1 - Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization

AU - Itagaki, Noriaki

AU - Kimura, Mari

AU - Sugahara, Tsutomu

AU - Iwabuchi, Yoshiharu

PY - 2005/9/15

Y1 - 2005/9/15

N2 - (Chemical Equation Presented) The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and encto-7-hydroxybicyclo[3.2.1]octan- 2-one, featuring an α-amino acid catalyzed intramolecular aldolization of σ-symmetric substrates, are described. A high enantioselectivity and a high catalytic efficiency have been exhibited by (4R,2S)-tetrabutylammonium 4-TBDPSoxy-prolinate in the aldolization of 3-(4-oxocyclohexyl)propionaldehyde to give highly enantiomerically enriched (1S,5R,8R)-8-hydroxybicyclo[3.3.1] nonan-2-one.

AB - (Chemical Equation Presented) The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and encto-7-hydroxybicyclo[3.2.1]octan- 2-one, featuring an α-amino acid catalyzed intramolecular aldolization of σ-symmetric substrates, are described. A high enantioselectivity and a high catalytic efficiency have been exhibited by (4R,2S)-tetrabutylammonium 4-TBDPSoxy-prolinate in the aldolization of 3-(4-oxocyclohexyl)propionaldehyde to give highly enantiomerically enriched (1S,5R,8R)-8-hydroxybicyclo[3.3.1] nonan-2-one.

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Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization

Abstract

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