期刊
TETRAHEDRON
卷 64, 期 42, 页码 9992-9998出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.07.080
关键词
diazaborolidines; chiral diamines; microwave irradiation; organocatalysis; asymmetric reduction
资金
- Conacyt, Mexico [45,157-Q]
A series of chiral diazaborolidine catalysts are readily prepared in situ at 75 degrees C in toluene solvent and under microwave irradiation (100 W, 15 min, air cooling) using chiral diamines derived from inexpensive and commercially available (S)-proline and borane-dimethyl sulfide. Special mention deserves the synthesis of potentially versatile diamine (S)-8 [(S)-(pyrrolidin-2-yl)diphenylmethanamine], with the key step being the conversion of tertiary alcohol (S)-(1-benzylpyrrolidin-2-yl)diphenyl methanol, (S)-12, to azide (S)-13. The chiral diazaborolidine/BH3 reagent system was successfully employed in the enantioselective reduction of prochiral ketones to give the corresponding secondary alcohols in excellent yield and with up to 96% enantiomeric purities. (C) 2008 Elsevier Ltd. All rights reserved.
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