ChemInform Abstract: Nucleophilic Addition of Triethyl Phosphite to Acetates of the Baylis- Hillman Adducts: Stereoselective Synthesis of (E)- and (Z)- Allylphosphonates.

ChemInform ◽  
2010 ◽  
Vol 27 (21) ◽  
pp. no-no
Author(s):  
D. BASAVAIAH ◽  
S. PANDIARAJU
Keyword(s):  
Nucleophilic Addition ◽  
Stereoselective Synthesis ◽  
Triethyl Phosphite

Stereoselective Synthesis of 3-Substituted and 3,4-Disubstituted Piperidine und Piperidin-2-one Derivatives

2012 ◽  
Vol 67 (4) ◽  
pp. 389-405 ◽  
Author(s):  
Ellen Klegraf ◽  
Horst Kunz
Keyword(s):  
Nucleophilic Addition ◽  
Stereoselective Synthesis ◽  
Organometallic Reagents

The stereoselective synthesis of 3-substituted and 3,4-disubstituted piperidine and piperidin-2-one derivatives was achieved starting from 2-pyridone. After N-galactosylation and subsequent O-silylation, nucleophilic addition of organometallic reagents proceeded with high regio- and stereoselectivity at 4-position. Substituents at position 3 were stereoselectively introduced by reaction of electrophiles with amide enolates of the N-galactosyl-2-piperidones.

Stereoselective synthesis of fully substituted ethylenes via an Ag-catalyzed 1,6-nucleophilic addition/annulation cascade

2020 ◽  
Vol 56 (56) ◽  
pp. 7749-7752
Author(s):  
Bu-Zheng Tang ◽  
Wen-Juan Hao ◽  
Jia-Zhuo Li ◽  
Shan-Shan Zhu ◽  
Shu-Jiang Tu ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Stereoselective Synthesis ◽  
First Time

A catalytic 1,6-nucleophilic addition/annulation cascade was developed for the first time, and used to produce 27 hitherto unreported ethylene-linked 1-naphthol-imidazole pairs with generally good yields and complete stereoselectivity.

Stereoselective Synthesis of Secondary Alkyllithiums and Their Application to Stereoselective Cuprations or Intramolecular Carbolithiations for the Stereoselective Synthesis of Alkylidene­cyclobutanes

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3141-3154 ◽  
Author(s):  
Kohei Moriya ◽  
Kuno Schwärzer ◽  
Konstantin Karaghiosoff ◽  
Paul Knochel
Keyword(s):  
Stereoselective Synthesis ◽  
Triethyl Phosphite ◽  
Significant Loss ◽  
Very High ◽  
Acylation Reactions

Secondary alkyllithium reagents were prepared stereoselectively via an iodo–lithium exchange by using tert-butyllithium. The resulting secondary alkyllithiums were converted directly into the corresponding alkylcopper reagents by transmetalation with copper(I) bromide–triethyl phosphite [CuBr·P(OEt)3] with retention of configuration and without significant loss of stereoselectivity. The resulting alkylcopper reagents were used for carbocupration or acylation reactions. In addition, a new intramolecular carbolithiation of secondary alkyllithium reagents possessing a remote alkyne moiety was also investigated, allowing the stereoselective production of alkylidenecylobutane derivatives with very high stereocontrol.

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