A synthetic strategy for tricholomic acid and acivicin

1987 ◽  
Vol 65 (1) ◽  
pp. 195-199 ◽  
Author(s):  
Stephen Hanessian ◽  
Benoit Vanasse
Keyword(s):  
Malic Acid ◽  
Aldol Condensation ◽  
Optically Active ◽  
Asymmetric Induction ◽  
Bond Forming ◽  
Synthetic Strategy

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.

Nickel-Catalyzed Electronically-Reversed Enantioselective Hydrocarbofunctionalizations of Acrylamides

Synlett ◽  
2021 ◽  
Author(s):  
Lou Shi ◽  
Wei Shu
Keyword(s):  
Nickel Catalyst ◽  
Functional Group ◽  
Optically Active ◽  
Forming Process ◽  
Carbon Bond ◽  
Bond Forming ◽  
Synthetic Strategy ◽  
Carbon Carbon Bond ◽  
Wide Range ◽  
Simple Protocol

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.

Engaging Zwitterions in Carbon−Carbon and Carbon−Nitrogen Bond-Forming Reactions:  A Promising Synthetic Strategy

2006 ◽  
Vol 39 (8) ◽  
pp. 520-530 ◽  
Author(s):  
Vijay Nair ◽  
Rajeev S. Menon ◽  
A. R. Sreekanth ◽  
N. Abhilash ◽  
A. T. Biju
Keyword(s):  
Bond Forming ◽  
Synthetic Strategy ◽  
Bond Forming Reactions ◽  
Nitrogen Bond

scholarly journals Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ6-sulfanyl)acetic acid esters with aldehydes

2018 ◽  
Vol 14 ◽  
pp. 373-380 ◽  
Author(s):  
Anna-Lena Dreier ◽  
Andrej V Matsnev ◽  
Joseph S Thrasher ◽  
Günter Haufe
Keyword(s):  
Acetic Acid ◽  
Aldol Condensation ◽  
Aldol Reactions ◽  
Complex Structures ◽  
Bond Forming ◽  
Hydroxyalkanoic Acid ◽  
Mukaiyama Aldol ◽  
Substituted Benzaldehydes ◽  
Acetic Acid Esters ◽  
Acid Esters

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.

ChemInform Abstract: CATALYTIC ASYMMETRIC INDUCTION IN OXIDATION REACTIONS. THE SYNTHESIS OF OPTICALLY ACTIVE EPOXIDES

1976 ◽  
Vol 7 (35) ◽  
pp. no-no
Author(s):  
R. HELDER ◽  
J. C. HUMMELEN ◽  
R. W. P. M. LAANE ◽  
J. S. WIERING ◽  
H. WYNBERG
Keyword(s):  
Optically Active ◽  
Asymmetric Induction ◽  
Oxidation Reactions ◽  
Catalytic Asymmetric

Using metal-metal bond forming reactions as a synthetic strategy towards building polymers containing FeFe and FeSnFe bonds

1996 ◽  
Vol 524 (1-2) ◽  
pp. 289-291 ◽  
Author(s):  
Patrick McArdle ◽  
Lynn O'Neill ◽  
Desmond Cunningham ◽  
Anthony R. Manning
Keyword(s):  
Metal Bond ◽  
Bond Forming ◽  
Synthetic Strategy ◽  
Metal Metal ◽  
Bond Forming Reactions
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