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Aminohaloborane in organic synthesis. VI. A simple enantioselective aldol synthesis by Tsutomu Sugasawa; Tatsuo Toyoda is a Chemistry article available to read on EtoBox.
What is Aminohaloborane in organic synthesis. VI. A simple enantioselective aldol synthesis about?
## Surmnary A simple asymmetric aldol condensation of acetophenone and benzaldehydes was performed via chiral vinylaminodichloroborane. The enatioselectivity was compared with that by a similar method using magnesium and lithium. Recently, Enders and his co-workers\* reported the first regiospecific and enantioselective aldol synthesis, which consists of a reaction series involving lithiation of chiral hydrazones followed by addition of carbonyl compounds, silylation of the condensation products and oxidative hydrolysis. We will describe here a much simpler enantioselective aldol synthesis as an extension of our simple directed aldol reaction using N-cyclohexylvinylaminodichloroborane. 3 Namely, (S)-(-)-N-(cc-methylbenzyliden)isobornylamine (la) was treated with boron trichloride in the presence of 2.5 equivalents of triethylamine in dichloromethane followed by addition of benzaldehyde. The reaction proceeded presumably via chiral vinylaminodichloroboranc 2. The optical purity (47.7%) and absolute configuration (R) of the aldol product (3a) obtained after acidic work-up followed by chromatography were determined by comparing the specific rotation of the corresponding acetyl derivat
Who reads Aminohaloborane in organic synthesis. VI. A simple enantioselective aldol synthesis?
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- Author
- Tsutomu Sugasawa; Tatsuo Toyoda
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)
- Published
- 1979
- Language
- EN
- Field
- Chemistry (Physical Sciences)