Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates
نویسندگان
چکیده
منابع مشابه
Synthesis of Fmoc-protected trans-4-methylproline.
Fmoc-protected trans-4-methylproline was synthesized starting from D-serine. The chiral scaffold of serine in the form of olefinated Garner's aldehyde 3 was used to control the diastereoselective formation of the new stereocenter on the hydrogenation of allylic alcohol 4. The diastereoselectivity (syn/anti ratio) of the process was 86:14, attained with Raney nickel. Hydrogen migration seems not...
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Positional isomers of naturally occurring peptide subunits were synthesized via highly diastereoselective reduction of tert-butylsulfinyl ketimines as a key reaction. While NaBH4 reduction of ketimines derived from 2-thiazolyl ketones afforded the (RS,R)-isomer with moderate diastereoselectivity, L-Selectride® reduction afforded the (RS,S)-isomer as the sole product. In contrast, ketimines deri...
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ژورنال
عنوان ژورنال: RSC Advances
سال: 2019
ISSN: 2046-2069
DOI: 10.1039/c9ra06827a