## Stereoselective Grignard-Type Reactions of Chiral N,N-Dibenzylamino Ketones. -Enantiomerically pure N,N-dibenzylamino ketones (I), derived from chiral ฮฑ-amino acids, react under nonchelating conditions with organometal reagents of type RLi, RMgX, RCeCl 2 . The reactions proceed highly diastere
Stereoselective Grignard-type reactions of chiral N,N-dibenzylamino ketones
โ Scribed by Manfred T. Reetz; Alfred Schmitz
- Book ID
- 104261153
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 230 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
N~V-Dibenzylamino ketones of the type Bn2N(RI)CHC(O)R 2, prepared in enantiomerically pure form from aamino acids, undergo non-chelation controlled Grignard-type reactions with RLi, RMgX or RCeCI2 without any undesired racemization.
๐ SIMILAR VOLUMES
N,N-Dibenzylamino ketones of the type Bn2N(R)CHC(O)CH3, prepared in enantiomericaUy pure form from ~amino acids, undergo stereoselective reductive amination using PhCH2NHz/NaCNBH3 or NI-I4OAc/NaCNBH3 with formation of diastereo-and enantiomerically pure vicinal diamines Bn2N(R)CHCH(NHCH2Ph)CH3 or Bn
The boron-mediated aldol reactions of a range of chiral a-(N,N)-dibenzylamino ketones with aldehydes can be controlled to provide stereodefined adducts. Complementary induction can be achieved with c Hex 2 BCl/Me 2 NEt leading to preferential formation of the 1,2-anti-2,4-syn adducts, while Bu 2 BOT