- Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline
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Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N-methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields.
- Amedjkouh, Mohamed,Ahlberg, Per
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p. 2229 - 2234
(2007/10/03)
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- SYNTHETIC CONTROL LEADING TO CHIRAL COMPOUNDS
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A highly diastereoselective cross aldol reaction is developed using divalent tin enolates formed from stannous trifluoromethanesulfonate and carbonyl compounds.The reaction is extended to a highly enantioselective cross aldol reaction employing chiral dia
- Mukaiyama, Teruaki,Iwasawa, Nobuharu,Stevens, Rodney W.,Haga, Toru
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p. 1381 - 1390
(2007/10/02)
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- HIGHLY ENANTIOSELECTIVE ALDOL-TYPE REACTION OF 3-ACETYLTHIAZOLIDINE-2-THIONE WITH ACHIRAL ALDEHYDES
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A highly enantioselective aldol-type reaction forming various β-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehydes is achieved via divalent tin enolate employing chiral diamine derived from (S)-proline as a ligand.
- Iwasawa, Nobuharu,Mukaiyama, Teruaki
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p. 297 - 298
(2007/10/02)
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