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Eight new pinene based tridentate Schiff bases of (+)-(1S,2R,3S,5S)-3-amino-6,6-dimethylbicyclo[3.1.1]heptan-2-ol were synthesized from (+)-(α)-pinene. Copper complexes of these Schiff bases were prepared for asymmetric nitroaldol (Henry) reaction. Among the eight copper complexes, 3-methylsalicylaldehyde-derived [CuSBADBH-4]2 32 showed high chiral induction (85 % ee) for the catalytic asymmetric Henry reaction of 4-nitrobenzaldehyde. Under optimal reaction conditions, 1 mol% [CuSBADBH-4]2 32 catalyzed enantioselective Henry reaction of various aromatic and poly aromatic aldehydes afforded the corresponding (R)-β-hydroxy nitroalkanes with high ee (up to 92 %) and yield (up to 99 %).

The (+)-α-pinene derived N-protected amino acid (I) is used in the synthesis of several constrained pyrrolidine derivatives.

Some problems of the chemistry of coordination metal compounds with chiral ligands based on natural organic compounds, especially terpenes, are generalized. The results on the synthesis and study of the structure and properties of the chiral transition metal complexes with several groups of new “hybrid” ligands based on monoterpenes pinene, (+)-3-carene, and limonene and sesquiterpene caryophyllene are considered.

Six terpene spiroborate esters are synthesized and tested as catalyst in the title reaction.

A range of novel chiral Schiff base and amine compounds based on α-pinene is synthesized and used as ligands in the vanadium-catalyzed asymmetric oxidation of thioanisole (III).

Aromatic aldehydes add to β-pinene under Lewis acid catalyzed Prins reaction conditions and yield the corresponding homoallylic alcohols. The reactions proceed in poor yield when electron donating substituents are present on the aromatic ring.

3-Ketobutyrates 6, derived from chiral auxiliary alcohols 5 - themselves efficiently prepared from β-pinene 4 - were reduced with line borohydride, giving 3-hydroxybutyrates 7 with 2-70 % de, depending on the nature of aryl group in alcohols 5.

Novel chiral sulfides, derived from pinene, have been prepared, converted to sulfonium salts and treated with base and aldehydes to generate non-racemic epoxides. Low to moderate enantioselectivities were obtained in the product epoxides and this possibly occurred as a result of using diastereomeric mixtures of sulfonium salts. Dibenzyl substituted sulfonium salts were also prepared to avoid formation of diastereomers but upon treatment with base and an aldehyde this gave the Stevens rearrangement product instead of epoxide.

β-ionone and α-pinene oxides 1, 3 isomerize rapidly and selectively to 1-(1,2,2-trimethylcyclopent-1-yl)-pent-2-en-1,4-dione 2 and the industrialy important 2,2,3-trimethyl-3-cyclopentene acetaldehyde 4 . under the influence of catalytic amounts of aminium salts A,B . In order to find insights into the mechanism of our procedure, protic and Lewis acid-catalyzed rearrangements have also been reconsidered.

(1S,2S,3R,5S)- and (1S,2S,3R,5S)-3-Amino-2-hydroxypinane ( 1 and 2 ) were prepared from the corresponding α-pinene in optically pure form. They and their derivatives reacted with various organoborane compounds. A variety of chiral oxazaborolidines 3a-e and 4 were obtained in high yield

The synthesis and chemistry of the novel reagents and stereochemically defined taxane A-ring building blocks 7e–9e are described, providing the basis for the solution to problems previously encountered in the development of syntheses of taxol and its analogs based on pinene.

(−)-8-Norethyl, 1′-normethyl Etodolac (−)-7 was synthesized in ee up to 95% from a Friedel-Crafts alkylation reaction between tryptophol 4 and the chiral β-ketobutyrate 5h , followed by hydrolysis.

Several title compounds have been synthesized in good overall yields through highly stereoselective Wittig-Horner condensations of suitable phosphonates with enantiopure aldehydes easily obtained from α-pinene as chiral precursor. These products, presenting two asymmetric carbons, two or four prochiral centers, and appropriate chemical functions, are versatile precursors to a variety of cyclobutane amino acid derivatives.

Co(III) or Mn(III) ions that replace some 4 atom% of Al(III) sites in microporous aluminophosphate number 36 (AlPO-36) function as catalytically active centres for the production from benzaldehyde of acylperoxy radicals: these, in turn, in dry air (30 bar) convert cyclohexene, pinene, limonene and styrene to their corresponding epoxides and diols.

Chiral auxiliaries previously prepared from (-)-β---pinene (3), alcohols 5a-e and 6, were transformed into β---ketobutyrates 7a-e and 8 respectively. These compounds were stereoselectively reduced by NaBH4 in the presence of additives (MnCl2 or CaCl2), leading to the corresponding β-hydroxy butyrates 10a-e and 11 in good chemical yield and poor to moderate stereoselectivities (de 0%-60%). The configuration at the newly generated stereogenic center in 10a was determined to be S through its transformation into S-(+)-butanediol.

The reaction of nitroso chlorides of natural monoterpene hydrocarbons, 3-carene and α-pinene, with simple α,ω-diamines (1,2-diaminoethane, 1,3-diaminopropane, piperazine, 1,6-diaminohexane, diethylenetriamine) results in the formation of α-amino oximes and bis-α-amino oximes. The product structures were proved by spectroscopy. The procedures of separation and purification of diamino oximes and diamino dioximes are described. Detailed analysis of the 1H and 13C NMR spectra of the new chiral nitrogen-containing derivatives was carried out.

A series of new chiral tetrahydroquinoline ligands, derived from chiral α-pinene, were successfully synthesized. Iridium and palladium complexes of these ligands were proven to be efficient catalysts for enantioselective hydrogenation and allylic substitution reactions with moderate to excellent enantioselectivities (90–95% ee) and high yields.