- Dimethyl sulfoxide as a "methylene" source: Ru(ii) photo-catalysed facile synthesis of acetals from alcohols
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Acetals are important molecules with versatile reactivity and uses. For the first time a simple photo-catalysed facile synthesis of formaldehyde acetals is documented herein upon the reaction of alcohols with dimethyl sulfoxide under very mild conditions in the presence of air. The reactions require only 1 mol% of RuII(bpy)3Cl2 photocatalyst under blue LED irradiation (λ = 445 nm) to give good to excellent yields of the corresponding acetal products. Here DMSO acts as a "methylene" source.
- Talukdar, Ranadeep
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supporting information
p. 13334 - 13338
(2019/09/06)
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- Asymmetric induction through metalation of chiral dithioacetals and oxathioacetals
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The work presented in this article consists of synthesis of chiral dithioacetals and oxathioacetals using pure chiral auxiliaries, such as, (+) camphor, (-) menthol, and L-cysteine. Metalation of these chiral dithioacetals and oxathioacetals, followed by nucleophilic addition to benzaldehyde and removal of chiral auxiliary, furnished scalemic mandelic acid with various enantiomeric purities. Copyright Taylor & Francis Group, LLC.
- Zaidi, Javid H.,Gunjial, Naseem Iqbal
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p. 2835 - 2845
(2008/03/11)
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- Synthesis of dithioacetals and oxathioacetals with chiral auxiliaries
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One-pot synthesis of dithioacetals as well as an efficient method for oxathioacetal is reported. Additionally, some chiral auxiliaries were used to synthesize enantiomerically pure dithioacetals and oxathioacetals.
- Zaidi, Javid H.,Naeem, Fazal,Khan, Khalid M.,Iqbal, Rasfaid,Zia-Ullah
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p. 2641 - 2653
(2007/10/03)
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- Preparation and Use of Chloromethyl (-)-Menthyl Ether in the Synthesis of Optically Pure α-Branched α-Amino Nitriles
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The synthesis of optically pure chloromethyl (-)-menthyl ether (2b) and its use in the synthesis of di-(-)-menthyl acetal (-)-menthyl (+)-menthyl acetals are described.The diastereomeric mixed acetals 7a,b and 8a,b are easily obtainable from the nitrones 5 and 6, KCN and 2b.The mixture of diastereomers are separated into the pure components 7a, 7b and 8a, 8b by simple silica gel column chromatography.Hydrolysis of these products (H2O2/Na2CO3, ultrasound) followed by N-O cleavage affords the heterocyclic α-methyl-α-amino amides 11a, 11b and 12a, 12b.These are subsequently hydrolyzed to give the corresponding α-methyl-α-amino acids with S and R configuration, respectively.
- Shatzmiller, Shimon,Dolithzky, Ben-Zion,Bahar, Eliezer
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p. 375 - 379
(2007/10/02)
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- DIMETHYLBORON BROMIDE AND DIPHENYLBORON BROMIDE. ACETAL AND KETAL CLEAVAGE. CLEAVAGE OF MEM, MOM AND MTM ETHERS.
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A general and efficient procedure for the cleavage of acetals and ketals by the use of dimethylboron bromide or diphenylboron bromide is described.Under similar reaction conditions, MEM, MOM and MTM ethers also react to afford the parent alcohols in excellent yields.
- Quindon, Yvan,Morton, Howard E.,Yoakim, Christiane
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p. 3969 - 3972
(2007/10/02)
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