Diastereoselectivity in prebiotically relevant 5(4H)-oxazolone-mediated peptide couplings.
نویسندگان
چکیده
A stereochemical study of a potentially prebiotic peptide-forming reaction was carried out as the first part of a systems chemistry investigation of potential paths for symmetry breaking. Substantial diastereomeric excesses result from a fast epimerization of the 5(4H)-oxazolone intermediate in aqueous solution.
منابع مشابه
Diastereoselective synthesis of vicinal tertiary and N-substituted quaternary stereogenic centers by catalytic hydroalkylation of dienes
An efficient and diastereoselective (CDC)–Rh-catalyzed hydroalkylation of dienes with 1,3-oxazol-5(4H)ones is reported. Aryl and alkyl substituted dienes are converted to a,a-substituted oxazolones (24 examples) by the formation of N-substituted quaternary carbon stereogenic centers in good yields (up to 96%) and with high diastereoselectivity (>20 : 1 dr). The reaction is tolerant of a range o...
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ورودعنوان ژورنال:
- Chemical communications
دوره 50 23 شماره
صفحات -
تاریخ انتشار 2014