51154-96-2Relevant articles and documents
Copper(I)-catalyzed enantioselective synthesis of α-chiral linear or carbocyclic (e)-(γ-alkoxyallyl)boronates
Yamamoto, Eiji,Takenouchi, Yuta,Ozaki, Taichi,Miya, Takanori,Ito, Hajime
, p. 16515 - 16521 (2014)
A new method has been developed for the catalytic asymmetric synthesis of α-chiral linear or carbocyclic (γ-alkoxyallyl)boronates via the copper(I)-catalyzed γ-boryl substitution of allyl acetals. This reaction afforded the products in high yields with ex
Organocatalytic enantioselective approach to the synthesis of verbalactone and (R)-massoialactone
Harbindu, Anand,Kumar, Pradeep
, p. 1954 - 1959 (2011)
The organocatalytic enantioselective synthesis of verbalactone and (R)-massoialactone is described. The requisite stereogenic centers of the target molecules were constructed using l-proline-catalyzed -aminoxylation and Horner-Wadsworth-Emmons (HWE) olefination. Yamaguchi macrolactonization and ring-closing metathesis were employed as key steps in the syntheses. Georg Thieme Verlag Stuttgart - New York.
General, Highly Selective Synthesis of 1,3- and 1,4-Difunctionalized Building Blocks by Regiodivergent Epoxide Opening
Funken, Nico,Mühlhaus, Felix,Gans?uer, Andreas
, p. 12030 - 12034 (2016)
We describe a regiodivergent epoxide opening (REO) featuring a catalyst-controlled synthesis of enantiomerically and diastereomerically highly enriched or pure syn- and anti- 1,3- and 1,4-difunctionalized building blocks from a common epoxide precursor. The REO is attractive for natural product synthesis and as a branching reaction for diversity-oriented synthesis with epoxides.
Preparation method of (R)-(-)-massoialactone
-
Paragraph 0057; 0059-0062, (2019/12/25)
The invention discloses a preparation method of (R)-(-)-massoialactone. The preparation method includes the following steps: in a solvent, under the action of a copper salt, an alkali and a ligand, beta,gamma-unsaturated ester and n-hexanal are subjected to a reaction shown in the specification to obtain (R)-(-)-massoalactrone; the copper salt is Cu(CH3CN)4PF6 or the alkali is Barton's Base, alkali metal tert-butanol salt or the ligand is (R,R)-Ph-BPE or (S)-DTBM-SEGPHOS. (R)-(-)-massoialactone can be obtained by one-step reaction with high yield and ee value; compared with other methods in the prior art, the method has many advantages, such as simple route, easy access to raw materials, mild conditions and the like, and has obvious advantages.
Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent
Matsumoto,Oohana,Hashimoto,Usuda,Shimoda,Ohshima,Suzuki,Togawa
, p. 3981 - 3988 (2018/06/15)
We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction is also applicable to acetates with a longer chain, which has a double bond at the terminus. To demonstrate the applicability of this method, enantiomerically pure (R)-massoialactone, a natural coconut flavor, has been synthesized from racemic 2-acetoxypent-4-enyl tosylate in several steps. Furthermore, the enzyme can recognize the stereochemistry of olefins, and the (Z)-alkenyl structure is more suitable for the enantioselective hydrolysis than the (E)-isomer.
