55170-74-6Relevant articles and documents
Asymmetric Evans syn-Aldol Reactions of Terpene-Derived Enals: Scope and Limitations
Kriening, Sebastian,Evagelou, Athanasios,Claasen, Birgit,Baro, Angelika,Laschat, Sabine
, p. 6720 - 6733 (2014)
The (E)- and (Z)-terpene-based aldehydes 6b and 6c with a silyl ether function in the γ-position were prepared and investigated in boron-mediated asymmetric Evans aldol reactions. Screening experiments of chiral N-acylated oxazolidinones 7, which are conveniently accessible from 5-methyl-5-hexenoic acid and Evans oxazolidinone auxiliaries, with various boron triflates and terpenoid neral (Z)-6a as aldehyde component, provided conditions in which highly selective formation of syn-aldol adduct 5a occurred and competing C=C double bond isomerization to 10 was completely suppressed. Applying the optimized conditions to O-silylated aldehydes 6b and 6c and N-acyloxazolidinone derivative (R)-7a confirmed the syn-selectivity and gave the appropriate products syn-5b,c and syn-21b,c in good yields. In the case of neral-derived syn adduct 5a, the configuration of the new stereogenic centers C-2/C-3 could be assigned as (2R,3S). The asymmetric Evans aldol reaction could be successfully applied to terpene-based (E)- and (Z)-aldehydes and N-acyloxazolidinones, giving syn-aldol adducts with high selectivity. Isomerization at the double bond was not observed.
CANNABINOID DERIVATIVES AND PRECURSORS, AND ASYMMETRIC SYNTHESIS FOR SAME
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, (2021/03/19)
The present disclosure relates to new cannabinoid derivatives and precursors and catalytic asymmetric processes for their preparation. The disclosure also relates to pharmaceutical compositions and pharmaceutical and analytical uses of the new cannabinoid derivatives. For instance, the disclosure relates to the preparation of new precursors, and the use of such precursor compounds for the preparation of isotope labelled cannabinoid products using chiral and achiral catalysts and catalytic processes. The deuterium, carbon-13 and carbon-14 containing compounds can be prepared and purified prior to transformation to the desired individual deuterated cannabinoid products.
SYNTHESIS OF CANNABINOIDS
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, (2019/02/05)
Provided are synthesis processes and intermediates for preparing cannabinoids and analogs.