79568-67-5Relevant academic research and scientific papers
Catalytic Generation and Chemoselective Transfer of Nucleophilic Hydrides from Dihydrogen
Pape, Felix,Brechmann, Lea T.,Teichert, Johannes F.
supporting information, p. 985 - 988 (2019/01/04)
Copper(I)–N-heterocyclic-carbene (NHC) complexes enabled the catalytic generation of nucleophilic hydrides from dihydrogen (H2) and their subsequent transfer to allylic chlorides. The highly chemoselective catalyst displayed no concomitant hydrogenation reactivity; in fact, the terminal double bond formed in the hydride transfer remained intact. Switching to deuterium gas (D2) allowed for regioselective monodeuteration with excellent isotope incorporation.
Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides
Soltanzadeh, Bardia,Jaganathan, Arvind,Staples, Richard J.,Borhan, Babak
supporting information, p. 9517 - 9522 (2015/08/11)
An organocatalytic and highly regio-, diastereo-, and enantioselective intermolecular haloetherification and haloesterification reaction of allyl amides is reported. A variety of alkene substituents and substitution patterns are compatible with this chemistry. Notably, electronically unbiased alkene substrates exhibit exquisite regio- and diastereoselectivity for the title transformation. We also demonstrate that the same catalytic system can be used in both chlorination and bromination reactions of allyl amides with a variety of nucleophiles with little or no modification. A highly regioselective intermolecular haloetherification that proceeds with excellent enantioselectivity, catalyzed by cinchona alkaloid dimers, is reported. The regioselectivity is preserved for unbiased alkyl substituted allyl amides with either E or Z geometry. (DHQD)2PHAL=hydroquinidine 1,4-phthalazinediyl diether.
Total synthesis and biological evaluation of halipeptins A and D and analogues
Nicolaou,Lizos, Dimitrios E.,Kim, David W.,Schlawe, Daniel,De Noronha, Rita G.,Longbottom, Deborah A.,Rodriquez, Manuela,Bucci, Mariarosaria,Cirino, Giuseppe
, p. 4460 - 4470 (2007/10/03)
The marine-derived halipeptins A (1a) and D (1d) and their analogues 3a, 3d and 4a, 4d were synthesized starting from building blocks 10, 13, 14a or 14d, 15, and 16. The first strategy for assembling the building blocks, involving a macrolactamization rea
Total synthesis of halipeptins A and D and analogues
Nicolaou,Kim, David W.,Schlawe, Daniel,Lizos, Dimitrios E.,De Noronha, Rita G.,Longbottom, Deborah A.
, p. 4925 - 4929 (2007/10/03)
(Chemical Equation Presented) Deceptive rings: Halipeptins A (1 a) and D (1 b) and analogues thereof were synthesized from fragments 2 and 3 a, b, respectively. Key steps included peptide-bond formation, DAST-induced thiazoline construction, and macrolact
Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes
Nacro,Baltas,Gorrichon
, p. 14013 - 14030 (2007/10/03)
Aldol condensations on α,β-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and syn γ,δ-epoxy β-hyd
