Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products
نویسندگان
چکیده
Since its introduction to the synthetic community in 1984, Garner's aldehyde has gained substantial attention as a chiral intermediate for the synthesis of numerous amino alcohol derivatives. This review presents some of the most successful carbon chain elongation reactions, namely carbonyl alkylations and olefinations. The literature is reviewed with particular attention on understanding how to avoid the deleterious epimerization of the existing stereocenter in Garner's aldehyde.
منابع مشابه
Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis †
2-Piperidineethanol (1) and its corresponding N-protected aldehyde (2) were used for the synthesis of several natural and synthetic compounds. The existence of a stereocenter at position 2 of the piperidine skeleton and the presence of an easily-functionalized group, such as the alcohol, set 1 as a valuable starting material for enantioselective synthesis. Herein, are presented both synthetic a...
متن کاملSynthesis of pyran and pyranone natural products.
An overview of the synthesis of the fungal metabolites (+)-dermolactone, (-)- semixanthomegnin, (+)- and (-)-mellein, (-)-ochratoxin alpha, (-)-(1R,3S)-thysanone, the enantiopure ventiloquinones L, E and G, and 8-desmethyleleutherin from a common chiral intermediate, is presented. Further methodology leading potentially toward extended quinones such as (3S,3'S)-xylindein is also outlined.
متن کاملNatural kaolin as an efficient recyclable catalyst for the synthesis of new 2,4-disubstituted quinolines
Substituted 2, 4- diphenyl quinolines were synthesized by a multicomponent domino reaction of anilines, aldehydes and terminal aryl alkynes. The synthetic pathway involves the formation of an imine, followed by the intermolecular addition of an alkyne to the imine. This intermediate immediately undergoes ring closure and oxidative aromatization. The reaction is catalyzed by natural kaolin, a st...
متن کاملNatural kaolin as an efficient recyclable catalyst for the synthesis of new 2,4-disubstituted quinolines
Substituted 2, 4- diphenyl quinolines were synthesized by a multicomponent domino reaction of anilines, aldehydes and terminal aryl alkynes. The synthetic pathway involves the formation of an imine, followed by the intermolecular addition of an alkyne to the imine. This intermediate immediately undergoes ring closure and oxidative aromatization. The reaction is catalyzed by natural kaolin, a st...
متن کاملTunable Phosphoramidite Ligands for Asymmetric Hydrovinylation: Ligands par excellence for Generation of All-Carbon Quaternary Centers.
1-Alkylstyrenes undergo efficient hydrovinylation (addition of ethylene) in the presence of a Ni-catalyst prepared from [(allyl)NiBr](2), Na(+) [BAr(4)](-) (Ar = 3,5-bis-trifluromethylphenyl), and a phosphoramidite ligand giving products in excellent yields and enantioselectivities. In many cases phosphoramidites derived from achiral 2,2'-biphenol are almost as good as ligands derived from the ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 9 شماره
صفحات -
تاریخ انتشار 2013