Enantioselective Synthesis of Apoptolidinone (I): Exploiting the Versatility of Thiazolidinethione Chiral Auxiliaries.

ChemInform ◽  
2006 ◽  
Vol 37 (9) ◽  
Author(s):  
Michael T. Crimmins ◽  
Hamish S. Christie ◽  
Kleem Chaudhary ◽  
Alan Long
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Auxiliaries

Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer

Synlett ◽  
2021 ◽  
Author(s):  
Jiangchun Zhong ◽  
Gucheng Yuan ◽  
Jiawei Liu ◽  
Shihang Yu ◽  
Xueyang Wang ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Enantioselective Synthesis ◽  
Synthetic Approach ◽  
Chiral Auxiliaries ◽  
Synthetic Sex Pheromone ◽  
Key Steps

AbstractThe synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans’ chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.

Asymmetric Friedel-Crafts reaction mediated by new chiral auxiliaries derived from (1S)-(−)-β-pinene: Enantioselective synthesis of (−)-8-Norethyl, 1′-normethyl Etodolac

1997 ◽  
Vol 38 (40) ◽  
pp. 7021-7024 ◽  
Author(s):  
Paulo R.R. Costa ◽  
Lúcio M. Cabral ◽  
Karla G. Alencar ◽  
Luciana L. Schmidt ◽  
Mário L.A.A. Vasconcellos
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Auxiliaries

Enantioselective synthesis of beta-amino acids using hexahydrobenzoxazolidinones as chiral auxiliaries

2008 ◽  
Vol 19 (24) ◽  
pp. 2839-2849 ◽  
Author(s):  
Gloria Reyes-Rangel ◽  
Erika Jiménez-González ◽  
José Luis Olivares-Romero ◽  
Eusebio Juaristi
Keyword(s):  
Amino Acids ◽  
Enantioselective Synthesis ◽  
Chiral Auxiliaries

Camphor-derived alcohols as chiral auxiliaries for asymmetric Pauson-Khand bicyclizations. Enantioselective synthesis of α-methoxyenones

1992 ◽  
Vol 433 (3) ◽  
pp. 305-310 ◽  
Author(s):  
Xavier Verdaguer ◽  
Albert Moyano ◽  
Miquel A. Pericàs ◽  
Antoni Riera ◽  
Andrew E. Greene ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Auxiliaries

Novel enantioselective synthesis of (S)-ketamine using chiral auxiliary and precursor Mannich base

2019 ◽  
Vol 97 (5) ◽  
pp. 331-336 ◽  
Author(s):  
Seyed Jamaladdin Gohari ◽  
Abdollah Javidan ◽  
Abolghasem Moghimi ◽  
Mohammad Javad Taghizadeh ◽  
Maryam Iman
Keyword(s):  
Acid Solution ◽  
Nucleophilic Addition ◽  
Grignard Reagent ◽  
Mannich Base ◽  
Enantioselective Synthesis ◽  
Chiral Auxiliary ◽  
Chiral Auxiliaries ◽  
Anesthetic Drug ◽  
Directing Group ◽  
High Yields

Ketamine has been extensively used as an anesthetic drug. Chiral auxiliaries such as tert-butanesulfinamide (TBSA) can be used for the asymmetric synthesis of (S)-ketamine. Condensation of TBSA with ketones provides tert-butanesulfinylimines in consistently high yields. The tert-butanesulfinyl group actuates the imine for nucleophilic addition, is a potent chiral directing group, and after nucleophilic addition is easily dissociated by intervention with acid solution. To prepare 2-(N-piperidinomethyl)-1-phenylcyclohexylamine (1), we started with the cyclohexanone and using Mannich reaction achieved an aminoketone. Then, we made the sulfiniylamin (2) by the condensation of TBSA with aminoketone. By using salts such as Ti(OEt)4, we obtained N-tert-butanesulfinylketimine in 85% yield. Next, we provided a new chiral center (3) using Grignard reagent as nucleophile at −78 °C (80% yield). Finally, after many steps, the (S)-ketamine synthesized under ozonolysis conditions, with good yield and enantioselectivity (75% yield and 75% ee).

Enantioselective synthesis of either enantiomer of α-alkyl-α-hydroxy-α-phenylacetic acids using chiral auxiliaries

2005 ◽  
Vol 16 (10) ◽  
pp. 1837-1843 ◽  
Author(s):  
Salvador Pérez-Estrada ◽  
Selene Lagunas-Rivera ◽  
Marı́a Elena Vargas-Dı́az ◽  
Pedro Velázquez-Ponce ◽  
Pedro Joseph-Nathan ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Auxiliaries
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