Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues

Yu-You Hsieh; Arun Raja; Bor-Cherng Hong; Prakash Kotame; Wan-Chen Chang; Gene-Hsiang Lee

doi:10.1021/acs.joc.7b02178

Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues

Yu-You Hsieh, Arun Raja, Bor-Cherng Hong, Prakash Kotame, Wan-Chen Chang, Gene-Hsiang Lee

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

20 Scopus citations

Abstract

A domino reaction with the organocatalytic enantioselective Michael-acetalization-Henry reaction of 2-hydroxynitrostyrene and 5-oxohexanal was developed for the synthesis of hexahydro-6H-benzo[c]chromenones with four consecutive stereogenic centers and high enantioselectivity (up to >99% ee). The transformation of a NaBH4-reduced adduct to the aflatoxin system via the Nef-cyclization process was achieved by the assistant of ZnBr2.

Original language	English
Pages (from-to)	12840-12848
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	82
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.7b02178
State	Published - 1 Dec 2017
Externally published	Yes

Keywords

Acetals/chemistry
Aflatoxins/chemistry
Catalysis
Chromones/chemistry
Hydroxy Acids/chemistry
Molecular Structure
Nitro Compounds/chemistry
Organic Chemicals
Stereoisomerism
Styrene/chemistry

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10.1021/acs.joc.7b02178

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Hsieh, Y.-Y., Raja, A., Hong, B.-C., Kotame, P., Chang, W.-C., & Lee, G.-H. (2017). Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues. Journal of Organic Chemistry, 82(23), 12840-12848. https://doi.org/10.1021/acs.joc.7b02178

Hsieh, Yu-You ; Raja, Arun ; Hong, Bor-Cherng et al. / Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 23. pp. 12840-12848.

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title = "Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues",

abstract = "A domino reaction with the organocatalytic enantioselective Michael-acetalization-Henry reaction of 2-hydroxynitrostyrene and 5-oxohexanal was developed for the synthesis of hexahydro-6H-benzo[c]chromenones with four consecutive stereogenic centers and high enantioselectivity (up to >99\% ee). The transformation of a NaBH4-reduced adduct to the aflatoxin system via the Nef-cyclization process was achieved by the assistant of ZnBr2.",

keywords = "Acetals/chemistry, Aflatoxins/chemistry, Catalysis, Chromones/chemistry, Hydroxy Acids/chemistry, Molecular Structure, Nitro Compounds/chemistry, Organic Chemicals, Stereoisomerism, Styrene/chemistry",

author = "Yu-You Hsieh and Arun Raja and Bor-Cherng Hong and Prakash Kotame and Wan-Chen Chang and Gene-Hsiang Lee",

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doi = "10.1021/acs.joc.7b02178",

language = "English",

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Hsieh, Y-Y, Raja, A, Hong, B-C, Kotame, P, Chang, W-C & Lee, G-H 2017, 'Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues', Journal of Organic Chemistry, vol. 82, no. 23, pp. 12840-12848. https://doi.org/10.1021/acs.joc.7b02178

Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues. / Hsieh, Yu-You; Raja, Arun; Hong, Bor-Cherng et al.
In: Journal of Organic Chemistry, Vol. 82, No. 23, 01.12.2017, p. 12840-12848.

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

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AU - Chang, Wan-Chen

AU - Lee, Gene-Hsiang

PY - 2017/12/1

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KW - Acetals/chemistry

KW - Aflatoxins/chemistry

KW - Catalysis

KW - Chromones/chemistry

KW - Hydroxy Acids/chemistry

KW - Molecular Structure

KW - Nitro Compounds/chemistry

KW - Organic Chemicals

KW - Stereoisomerism

KW - Styrene/chemistry

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Hsieh YY, Raja A, Hong BC, Kotame P, Chang WC, Lee GH. Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues. Journal of Organic Chemistry. 2017 Dec 1;82(23):12840-12848. doi: 10.1021/acs.joc.7b02178