Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence† †Electronic supplementary information (ESI) available. CCDC 990847. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4cc01885k Click here for additional data file. Click here for additional data file.
نویسندگان
چکیده
A highly stereoselective one-pot procedure involving an enantioselective Michael addition promoted by low loading of an amino-squaramide catalyst followed by an achiral base catalyzed domino Michael-Knoevenagel-type 1,2-addition sequence provides efficient access to fully substituted cyclohexanes bearing five contiguous stereogenic centers in good yields (68-86%) and excellent stereoselectivities (>30 : 1 dr and 96-99% ee).
منابع مشابه
Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids† †Electronic supplementary information (ESI) available. CCDC 1487136. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc04522g Click here for additional data file. Click here for additional data file.
متن کامل
Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction† †Electronic supplementary information (ESI) available: Experimental procedures and characterization date (NMR, IR, MS, HPLC). CCDC 1437686. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5cc09581f Click here for additional data file. Click here for additional data file.
An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes bearing four contiguous stereocenters is described. A variety of α,β-unsaturated aldehydes and 2-nitroallylic acetates react well with good domino yields and high stereoselectivities.
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متن کامل
Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters† †Electronic supplementary information (ESI) available. CCDC 1037530. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4cc09730k
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Generation of 1,2-azaboretidines via reduction of ADC borane adducts† †Electronic supplementary information (ESI) available: Experimental, crystallographic, and computational details. CCDC 1042591–1042594. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc01077b Click here for additional data file. Click here for additional data file.
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