59614-85-6Relevant articles and documents
CuH-Catalyzed Asymmetric Conjugate Reductions of Acyclic Enones
Lipshutz, Bruce H.,Servesko, Jeff M.
, p. 4789 - 4792 (2003)
A powerful new reaction has been developed for the asymmetric 1, 4-reduction of prochiral enones (see scheme). The key ingredients in this exceedingly mild and straightforward procedure are catalytic quantities of CuH, a readily available nonracemic phosphane ligand such as that shown, and inexpensive polymethyl-hydrosiloxane (PMHS) as the stoichiometric source of hydride.
Syntheses of (R)- and (S)-3-methylheptanoic acids
Zhang, Shunji,Shi, Yong,Tian, Weisheng
supporting information, p. 674 - 678 (2015/06/25)
Starting from chiral methyl molecules 3 and 4, both derived from (R)-4-methyl-δ-valerolactone, we have accomplished the synthesis of (R) and (S)-3-methylheptanoic acids. Our methods are amendable to the syntheses of a wide variety of chiral 3-methyl alkanoic acids. Both enantiomers of 3-methylheptanoic acid have been synthesized from chiral methyl molecules which were derived from (R)-4-methyl-δ-valerolactone (5). A wide variety of chiral 3-methyl alkanoic acids can also be synthesized by the methods described herein.
Asymmetric cascade reaction sequences via chiral lithiated intermediates
Hogan, Anne-Marie L.,O'Shea, Donal F.
, p. 2503 - 2509 (2008/09/19)
(Chemical Equation Presented) The (-)-sparteine-mediated enantioselective intermolecular carbolithiation of (E)-2-propenylarylamines allows for the generation of chiral lithiated intermediates which have broad synthetic potential. These intermediates have been exploited in a series of further in situ reactions with electrophiles to generate a collection of products each containing a common stereogenic center. The stereogenic center, formed in high enantiomeric ratio in the first carbolithiation step, is carried through the cascade reaction sequence to the final products and is independent of electrophile used. The methodology is demonstrated by the synthesis of structurally diverse chiral anilines, indoles, and indolones all with an er of 92:8 (±1). The heterocyclic syntheses involve an enantioselective alkene carbolithiation and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole or indolone rings.