A synthetic strategy for tricholomic acid and acivicin

1987 ◽  
Vol 65 (1) ◽  
pp. 195-199 ◽  
Author(s):  
Stephen Hanessian ◽  
Benoit Vanasse

A synthetic strategy towards tricholomic acid and acivicin has been established using the aldol condensation of N-pyruvilideneglycinatoaquocopper(II) and an optically active aldehyde derived from S-malic acid as the key bond-forming reaction. Although a viable strategy was developed, no asymmetric induction was observed.

Synlett ◽  
2021 ◽  
Author(s):  
Lou Shi ◽  
Wei Shu

Asymmetric hydrocarbofunctionalizations of alkenes has emerged as an efficient synthetic strategy for accessing optically active molecules via carbon-carbon bond-forming process from readily available alkenes and carbo-electrophiles. Herein, we present a summary of the efforts from our group to control the regio- and enantioselectivity of hydrocarbofunctionalizations of electron-deficient alkenes with a nickel catalyst and chiral bisoxazolidine ligand. The reaction undergoes electron-reversed hydrocarbofunctionalizations acrylamides with excellent enantioselectivity. This operationally simple protocol enables the asymmetric hydroalkylation, hydrobenzylation and hydropropargylation of acrylamides. This reaction is useful for preparing a wide range of α-branched chiral amides with broad functional group tolerance.


2006 ◽  
Vol 39 (8) ◽  
pp. 520-530 ◽  
Author(s):  
Vijay Nair ◽  
Rajeev S. Menon ◽  
A. R. Sreekanth ◽  
N. Abhilash ◽  
A. T. Biju

2018 ◽  
Vol 14 ◽  
pp. 373-380 ◽  
Author(s):  
Anna-Lena Dreier ◽  
Andrej V Matsnev ◽  
Joseph S Thrasher ◽  
Günter Haufe

Aldol reactions belong to the most frequently used C–C bond forming transformations utilized particularly for the construction of complex structures. The selectivity of these reactions depends on the geometry of the intermediate enolates. Here, we have reacted octyl pentafluoro-λ6-sulfanylacetate with substituted benzaldehydes and acetaldehyde under the conditions of the silicon-mediated Mukaiyama aldol reaction. The transformations proceeded with high diastereoselectivity. In case of benzaldehydes with electron-withdrawing substituents in the para-position, syn-α-SF5-β-hydroxyalkanoic acid esters were produced. The reaction was also successful with meta-substituted benzaldehydes and o-fluorobenzaldehyde. In contrast, p-methyl-, p-methoxy-, and p-ethoxybenzaldehydes led selectively to aldol condensation products with (E)-configured double bonds in 30–40% yields. In preliminary experiments with an SF5-substituted acetic acid morpholide and p-nitrobenzaldehyde, a low amount of an aldol product was formed under similar conditions.


1976 ◽  
Vol 7 (35) ◽  
pp. no-no
Author(s):  
R. HELDER ◽  
J. C. HUMMELEN ◽  
R. W. P. M. LAANE ◽  
J. S. WIERING ◽  
H. WYNBERG

1996 ◽  
Vol 524 (1-2) ◽  
pp. 289-291 ◽  
Author(s):  
Patrick McArdle ◽  
Lynn O'Neill ◽  
Desmond Cunningham ◽  
Anthony R. Manning

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