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Aldol reactions of α-(N,N-dibenzylamino) ethyl ketones

✍ Scribed by Jane Betty Goh; Bharat R. Lagu; Julie Wurster; Dennis C. Liotta

Book ID
103406913
Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
312 KB
Volume
35
Category
Article
ISSN
0040-4039

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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

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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.

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## Stereoselective Grignard-Type Reactions of Chiral N,N-Dibenzylamino Ketones. -Enantiomerically pure N,N-dibenzylamino ketones (I), derived from chiral α-amino acids, react under nonchelating conditions with organometal reagents of type RLi, RMgX, RCeCl 2 . The reactions proceed highly diastere

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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