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Enantioselective Protonation of Simple Enolates: Chiral Imide as a Chiral Proton Source

✍ Scribed by Dr. Akira Yanagisawa; Takeshi Kuribayashi; Tetsuo Kikuchi; Prof. Hisashi Yamamoto

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
411 KB
Volume
33
Category
Article
ISSN
0044-8249

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✦ Synopsis

Dimeric [Ca(OCtBu,)

,] is synthesized from 2a and HOCIBU, by analogy to Equation (c); colorless crystals, moderately soluble in n-pentane. readily soluble in toluene and diethyl ether. Warming under high vacuum (185'Ci mbar) gives a moderate yield of trimeric [Ca(OCHtBu,),] as a colorless sublimate. soluble in toluene and THF. The properties of the sublimate are identical to those of a sample prepared from 2a and HOCHlB<u2.The trimeric structure of [C~(OCHIBU,),] results from chemical ionization (CI) mass spectrometry. a) W.

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Diastereoselective Protonation of Chiral Enolate with Chiral Imides. -Protonation of the lithium enolate (I) of (-)-menthone by chiral imides such as the (R)-imide of conditions (A) generates mainly the cis ketone (III). The selectivity of this process can be completely reversed by using the corres