Camphanoyl chloride

Because both enantiomers, (+) and (-)-camphoric add, are available by oxidation either from natural (+)-D-camphor or from natural (-)-L-borneol, both enantiomers of camphanoyl chloride can be prepared conveniently.3 5 The corresponding enantiomers of camphanic acid were described for the first time by Wreden6and Aschan.7 The three-step procedure, described above is an adaptation of procedures described by Aschan,8 Zelinsky et al.,9 Meyer et al.,10 and Gerlach.3... 

The preparation of enantiomerically pure chemicals is also the theme of the next group of four procedures. The biopolymer polyhydroxybutyric acid, which is now produced on an industrial scale, serves as the starting material for the large scale synthesis of (R)-3-HYDROXYBUTANOIC ACID and (R)-METHYL 3-HYDROXYBUTANOATE. Esters of (-)-camphanic acid are useful derivatives for resolving and determining the enantiomeric purity of primary and secondary alcohols. An optimized preparation of (-)-(1S,4R)-CAMPHANOYL CHLORIDE is provided. The preparation of enantiomerically pure a-hydroxyketones from ethyl lactate is illustrated in the synthesis of (3HS)-[(tert)-BUTYL-DIPHENYLSILYL)OXY]-2-BUTANONE. One use of this chiral a-hydroxyketone is provided in the synthesis of (2S,3S)-3-ACETYL-8-... 

In the presence of a catalytical amount of Znl2, (-)-l-cyanovinyl camphanate, derived from the commercially available (-)-(lS)-camphanoyl chloride and 2-oxopropionitrile, added to furan (an inexpensive starting material derived from the biomass ) and afforded a 45 45 5 5 mixture of adducts 32/40/41/42 in 90 % yield from which 32 could be isolated (98 % d.e.) in 29 % yield after repetitive... 

Camphanoyl chloride (1). Supplier Aldrich. Preparation from camphoric acid ... 

Derivatives of camphanic acid, such as esters or amides, are usually prepared by the reaction of camphanoyl chloride with suitable nucleophiles. Thus, the enol ester with 2-oxopropaneni-trile 72 was used as a chiral dienophile71. As chiral dienes for inverse Diels-Alder reactions, esters with the enolates of 1,3-diketones, e.g., 73, have been prepared72. Amides, such as 74 and 75, have been used for the synthesis of chiral aminophosphonic acids (Section D.8.) and for acyliminium reactions (Section D.1.4.5.). 

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