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T1 - Stereoselective synthesis of 1,2-cis galactosides

T1 - Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations

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Stereoselective Synthesis of Oxabicyclo[2.2.1]heptenes …

The regio-and stereoselective synthesis of allylsilane derivatives bearing a tetrasubstituted olefin was achieved using 2,2-diborylethylsilane as a key intermediate. The regioselective deprotonation of a 2,2-diborylethylsilane with LTMP and the subsequent nucleophilic addition to ketones gave corresponding allylsilanes in good to excellent yield with excellent stereoselectivity.

Stereoselective synthesis of 2-deoxy-β-glycosides using anomeric o-alkylation/arylation.

AB - The regio-and stereoselective synthesis of allylsilane derivatives bearing a tetrasubstituted olefin was achieved using 2,2-diborylethylsilane as a key intermediate. The regioselective deprotonation of a 2,2-diborylethylsilane with LTMP and the subsequent nucleophilic addition to ketones gave corresponding allylsilanes in good to excellent yield with excellent stereoselectivity.

Stereoselective Synthesis of 2,8 …

N2 - The regio-and stereoselective synthesis of allylsilane derivatives bearing a tetrasubstituted olefin was achieved using 2,2-diborylethylsilane as a key intermediate. The regioselective deprotonation of a 2,2-diborylethylsilane with LTMP and the subsequent nucleophilic addition to ketones gave corresponding allylsilanes in good to excellent yield with excellent stereoselectivity.

AB - An α-selective galactosylation was demonstrated under various conditions. Among these α-galactoside approaches, high α-selectivity was achieved by the virtue of 4,6-O-di-tert-butylsilylene (DTBS) group. Yield was further improved by the influence of a 2-O-benzylated donor compared to 2-O-benzoylated donor. This method was then applied to the first highly stereoselective synthesis of a newly found trisaccharide glycosphingolipid in Zygomycetes species.

Stereoselective synthesis of 2,3-unsaturated-O …

2,3-Dihydro-4-pyranones were synthesized stereoselectively using a chiral phosphine oxide as the catalyst. The phosphine oxide sequentially activated silicon tetrachloride and promoted the double aldol reaction of 4-methoxy-3-buten-2-one with aldehydes. Subsequent stereoselective cyclization afforded the corresponding highly functionalized 2,3-dihydro-4-pyranones bearing three contiguous chiral centers in good yields and with high diastereo- and enantioselectivities.

N2 - An α-selective galactosylation was demonstrated under various conditions. Among these α-galactoside approaches, high α-selectivity was achieved by the virtue of 4,6-O-di-tert-butylsilylene (DTBS) group. Yield was further improved by the influence of a 2-O-benzylated donor compared to 2-O-benzoylated donor. This method was then applied to the first highly stereoselective synthesis of a newly found trisaccharide glycosphingolipid in Zygomycetes species.

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  • Stereoselective heterocyclic synthesis / 2

    “Stereoselective Synthesis of Cis-2-aryl- and 2-alkyl-1-chlorocyclopropanecarboxaldehydes.” 43 (4): 599–602.

  • Get this from a library! Stereoselective heterocyclic synthesis / 2..

    Stereoselective synthesis of cis-2-aryl- and 2-alkyl-1-chlorocyclopropanecarboxaldehydes.

  • Stereoselective Synthesis of 2-Deoxy-β-glycosides …

    “Stereoselective Synthesis of Cis-2-aryl- and 2-alkyl-1-chlorocyclopropanecarboxaldehydes.” 43.4 (2002): 599–602.

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One-Pot Stereoselective Synthesis of Alkyl Z-2 …

AB - The stereoselective synthesis of an antifungal drug, Terbinafine, bearing (E)-tert-butylenyne structural element as the side chain is achieved by coupling N-methyl-1-napthalene methanamine with 1-bromo-6,6-dimethyl-2E-hepten-4- yne in good yield. The new methodology avoids the use of toxic starting materials like acrolein and phosphorous pentachloride that were used in earlier reports. The structure was confirmed by IR, NMR, MS, and elemental analysis.

Stereoselective synthesis of 1,2-13C2-L-fucose, 1,2 …

AB - A method for the synthesis of imidazolidin-2-ones from N-allylureas and aryl or alkenyl bromides via Pd-catalyzed carboamination reactions is described. The N-allylurea precursors are prepared in one step from readily available allylic amines and isocyanates, and the Pd-catalyzed reactions effect the formation of a C-C bond, a C-N bond, and up to two stereocenters in a single step. Good diastereoselectivities are obtained for the conversion of substrates bearing allylic substituents to 4,5-disubstituted imidazolidin-2-ones, and excellent selectivity for the generation of products resulting from syn-addition across the alkene is observed when substrates derived from cyclic alkenes or E-1,2-disubstituted alkenes are employed. A brief discussion of reaction mechanism and product stereochemistry is presented.

stereoselective synthesis - 702 course - Massey University

N2 - A method for the synthesis of imidazolidin-2-ones from N-allylureas and aryl or alkenyl bromides via Pd-catalyzed carboamination reactions is described. The N-allylurea precursors are prepared in one step from readily available allylic amines and isocyanates, and the Pd-catalyzed reactions effect the formation of a C-C bond, a C-N bond, and up to two stereocenters in a single step. Good diastereoselectivities are obtained for the conversion of substrates bearing allylic substituents to 4,5-disubstituted imidazolidin-2-ones, and excellent selectivity for the generation of products resulting from syn-addition across the alkene is observed when substrates derived from cyclic alkenes or E-1,2-disubstituted alkenes are employed. A brief discussion of reaction mechanism and product stereochemistry is presented.

Assymetric Induction - Home - Michigan State University

A highly efficient and stereoselective synthesis of coumarin-, 1,3-cyclohexanedione-, and 1,4-naphthoquinone-fused 2,8-dioxabicyclo[3.3.1]nonanes is described. This was achieved via a sequential Michael addition/bicyclization reaction from easily accessible 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one derivatives. Three chemical bonds (one C–C bond and two C–O bonds), two six-membered cycles, and two stereogenic centers were formed in a one-pot operation.

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