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The saccharide-based chiral bifunctional thiourea-phosphines were developed as chiral organocatalysts for the intramolecular Morita-Baylis-Hillman reaction of ω-formyl-enones. With only 2 mol% of thiourea-phosphine catalyst 3c, chiral functionalized cyclohexenes were achieved under mild reaction conditions with excellent yields and enantioselectivities. [ABSTRACT FROM AUTHOR]

The direct preparation of a kind of fluorinating reagent 1 [F-TEDA-N(SO2Ph)2] was realized in high yield via the complexation of N-fluorobenzenesulfonimide (NFSI) with 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium N′, N′-bis-(benzenesulfonylimide) salt. In its fluorination to oxindoles, the fluorinating products 6 were afforded in moderate to high yields. [ABSTRACT FROM AUTHOR]

Z and E configuration 4-aryl-but-2-en-1-ols were isolated from several terrestrial plants, and ( Z)-4-aryl-but-2en-1-ols were found to have choleretic activity. Strategies have been reported to synthesize ( E)-4-aryl-but-2-en-1ols with high selectivity. However, there is no method to obtain ( Z)-4-aryl-but-2-en-1-ols with high selectivity now. We developed a Suzuki-Miyaura cross-coupling reaction of 1,2-oxaborol-2(5 H)-ols with benzyl bromides to synthesize ( Z)-4-aryl-but-2-en-1-ols, the products were obtained in up to 94% isolated yield. [ABSTRACT FROM AUTHOR]

A class of bifunctional phosphinothioureas derived from saccharide was developed as new organocatalysts for the enantioselective Morita-Baylis-Hillman reaction between acrylates and aldehydes. With 10 mol% of glucose-based phosphinothiourea 1d, the allylic alcohols were obtained in up to 96% yield and 83% ee under mild reaction conditions. [ABSTRACT FROM AUTHOR]