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Mild and Practical Reductions of Prochiral Ketones to Chiral Alcohols Using the Chiral Boronic Ester TarB—H.
SYNTHESIS 2008, No. 23, pp 3874–3876xx.xx.2008 Advanced online publication: 06.11.2008 DOI: 10.1055/s-0028-1083605; Art ID: Z18008SS © Georg Thieme Verlag Stuttgart · New York Abstract: Chiral
Highly enantioselective and regioselective carbonyl reduction of cyclic alpha,beta-unsaturated ketones using TarB-NO2 and sodium borohydride.
Asymmetric 1,2-reduction of alpha,beta-unsaturated ketones using TarB-NO(2) and NaBH(4) is reported to yield chiral allylic alcohols in enantiomeric excess up to 99%.
Asymmetric Reductions Involving Borohydrides: A Practical Asymmetric Reduction of Ketones Mediated by (l)-TarB−NO2: A Chiral Lewis Acid
The asymmetric reduction of prochiral ketones has been achieved through a myriad of different methods. Early reductions gave low to moderate enantiomeric excesses (ee's), but more modern reagents
Mild and expedient asymmetric reductions of α,β-unsaturated alkenyl and alkynyl ketones by TarB-NO2 and mechanistic investigations of ketone reduction.
A facile and mild reduction procedure is reported for the preparation of chiral allylic and propargyl alcohols in high enantiomeric purity and it was found that highly branched aliphatic ynones were reduced with optimal induction up to 90% ee, while reduction of aromatic and linear aliphatics resulted in more modest enantioselectivity.
An ester enolate-Claisen rearrangement route to substituted 4-alkylideneprolines. studies toward a definitive structural revision of lucentamycin A.
The studies indicate that the Emp stereogenic centers are not the source of structural misassignment, and the current strategy should find broad utility in the synthesis of additional natural product analogues and related 3-alkyl-4-alksylidene prolines.
An Ester Enolate—Claisen Rearrangement Route to Substituted 4-Alkylideneprolines. Studies Toward a Definitive Structural Revision of Lucentamycin A.
In the presence of NaN(Tms)2, esters of type (I) and (IX) rearrange to amino acids like (II) and (X) with moderate to high diastereoselectivity.