150406-34-1Relevant articles and documents
Mild Deprotection of tert-Butyl and tert-Amyl Ethers Leading either to Alcohols or to Trialkylsilyl ethers
Franck, Xavier,Figadere, Bruno,Cave, Andre
, p. 711 - 714 (1995)
Tert-butyl and tert-amyl ethers afford the corresponding tert-butyldimethylsilyl ethers when treated by one equivalent of tert-butyldimethylsilyl triflate (TBDMSOTf), followed by one equivalent of 2,6-lutidine.However, treatment by a catalytic amount of TBDMSOTf without base, led to the corresponding free alcohols.
Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles
Tsukamoto, Hirokazu,Ito, Kazuya,Doi, Takayuki
supporting information, p. 5102 - 5105 (2018/05/26)
Multi-substituted dihydrofurans were obtained from a palladium-catalysed coupling reaction between 2,3-alkadienols and ketones bearing an electron-withdrawing group at the α-position. Methanol as a solvent was essential for the initial dehydrative substitution to suppress the competitive hydroalkylation of the diene moiety. The substitution would be followed by intramolecular hydroalkoxylation under the same catalysis.
Rhodium-catalyzed hydroformylation of 1,1-disubstituted allenes employing the self-assembling 6-DPPon system
K?pfer, Alexander,Breit, Bernhard
supporting information, p. 6913 - 6917 (2015/06/08)
Abstract A rhodium-catalyzed hydroformylation of 1,1-disubstituted allenes is reported. Using a RhI/6-DPPon catalyst system, one can obtain β,γ-unsaturated aldehydes in high regio- and chemoselectivity. The Z-configured product is formed with up to >95% selectivity when unsymmetrically 1,1-disubstituted allenes are submitted to the reaction conditions. This is the first time that these interesting building blocks are accessible by hydroformylation of allenes. The utility of this methodology is demonstrated by further transformations of one of the obtained products. β,γ-Unsaturated aldehydes are obtained by a rhodium-catalyzed hydroformylation of 1,1-disubstituted allenes. For unsymmetrically 1,1-disubstituted allenes the Z-configured product is formed in up to about 95% selectivity. This is the first time that these building blocks are accessible by hydroformylation of allenes. The utility of this methodology is demonstrated by further transformations of one of the obtained products.
Gold(I)-catalyzed rearrangement of alkynylaziridine indoles for the synthesis of spiro-tetrahydro-β-carbolines
Yang, Yan-Fang,Li, Lian-Hua,He, Yu-Tao,Luo, Jian-Yi,Liang, Yong-Min
supporting information, p. 702 - 707 (2014/02/14)
Functionalized spiro-tetrahydro-β-carbolines were formed by an efficient gold(I)-catalyzed rearrangement reaction of alkynylaziridine indoles. The reaction involved a Friedel-Crafts type intramolecular reaction of alkynylaziridine indoles, following by hydroamination of aminoallene intermediate.
Lipase-catalyzed highly enantioselective kinetic resolution of boron-containing chiral alcohols
Andrade, Leandro H.,Barcellos, Thiago
supporting information; experimental part, p. 3052 - 3055 (2009/12/05)
The first application of enzymes as catalysts to obtain optically pure boron compounds is described. The kinetic resolution of boron-containing chiral alcohols via enantioselective transesterification catalyzed by lipases was studied. Aromatic, allylic, and aliphatic secondary alcohols containing a boronate ester or boronic acid group were resolved by lipase from Candida antartica (CALB), and excellent E values (E > 200) and high enantiomeric excesses (up to >99%) of both remaining substrates and acetylated product were obtained.
Total synthesis and absolute stereochemical assignment of (+)- and (-)-galbulimima alkaloid 13
Movassaghi, Mohammad,Hunt, Diana K.,Tjandra, Meiliana
, p. 8126 - 8127 (2007/10/03)
We describe the total synthesis of (+)- and (-)-galbulimima alkaloid 13. The absolute stereochemistry of natural (-)-galbulimima alkaloid 13 is revised to 2S. Sequential use of catalytic cross-coupling and cross-metathesis reactions followed by an intramo
Synthesis of β-hydroxy ketones and vinylsilanes from homopropargylic alcohols by intramolecular hydrosilation
Marshall, James A.,Yanik, Mathew M.
, p. 2173 - 2175 (2007/10/03)
matrix presented Catalytic intramolecular hydrosilation of nonracemic homopropargylic alcohols affords the corresponding five-membered cyclic siloxanes regiospecifically. Oxidation or alkylmetal addition converts these intermediates into β-hydroxy ketones
A mild synthesis of substituted furans from -γ-hydroxy-α,β-unsaturated ketones
Sammond, Douglas M.,Sammakia, Tarek
, p. 6065 - 6068 (2007/10/03)
The acid-catalyzed cyclodehydration of (Z)- and (E)-γ-hydroxy-α,β-unsaturated ketones to furans is described. In the case of E olefins, photochemical trans- to cis-olefin isomerization was found to accelerate the reaction.
An Efficient and Versatile Synthesis of the Butenolide Subunit of 4-Hydroxylated Annonaceous Acetogenins
Hoye, Thomas R.,Humpal, Paul E.,Jimenez, Jorge I.,Mayer, Michael J.,Tan, Lushi,Ye, Zhixiong
, p. 7517 - 7520 (2007/10/02)
Title butenolides 2 have been synthesized by an efficient and versatile route that provides access to any stereoisomer by use of individual enantiomers of the precursors 3-butyn-2-ol and terminal epoxides.
