144899-42-3

Basic information

• Product Name: (S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine
• Synonyms: (S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine
• CAS NO: 144899-42-3
• Molecular Weight: 0
• Mol File: 144899-42-3.mol

Chemical Properties

• CAS DataBase Reference: (S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine(144899-42-3)
• EPA Substance Registry System: (S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine(144899-42-3)

Safety Data

• Hazardous Substances Data: 144899-42-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine is used as a chiral building block for the creation of complex organic molecules. Its unique structure and chiral nature allow for the development of novel compounds with specific properties and applications in various industries.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine is used as a chiral auxiliary for asymmetric synthesis. This application is crucial for the production of enantiomerically pure drugs, which can have significant implications for the effectiveness and safety of medications.
Used in Agrochemical Production:
(S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine is also utilized in the development of new agrochemicals. Its chiral properties enable the creation of more effective and targeted pesticides, herbicides, and other agricultural products.
Used in Catalyst Design:
(S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine is employed as a catalyst in certain chemical reactions, enhancing the efficiency and selectivity of these processes. This application is particularly relevant in the synthesis of complex molecules and the production of fine chemicals.

Upstream product

• 170918-41-9 (S)-2-amino-3-phenyl-1,1-dimethylpropanol 
• 67-64-1 acetone 
• 110480-86-9 (1S)-1-amino-2-methyl-1-phenylpropan-2-ol 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Downstream Products

• 155185-84-5 1-((S)-4-Benzyl-2,2,5,5-tetramethyl-oxazolidin-3-yl)-2-chloro-ethanone 
• 171736-88-2 (S)-4-benzyl-2,2,5,5-tetramethyl-3-propanoyloxazolidine 
• 265643-04-7 (2E,4S)-2,2,5,5-tetramethyl-3-(2-methyl-1-oxo-2-butenyl)-4-phenylmethyloxazolidine 
• 936347-55-6 (S)-(4-benzyl-2,2,5,5-tetramethyloxazolidin-3-yl)pyridin-3-yl-methanone 
• 155185-92-5 2-(Benzhydrylidene-amino)-1-((S)-4-benzyl-2,2,5,5-tetramethyl-oxazolidin-3-yl)-ethanone 
• 918830-50-9 1-((S)-4-benzyl-2,2,5,5-tetramethyloxazolidin-3-yl)ethanone 
• 171736-91-7 (S)-4-benzyl-3-methoxyacetyl-2,2,5,5-tetramethyloxazolidine 
• 1027188-98-2 (S)-4-Benzyl-3-cinnamoyl-2,2,5,5-tetramethyloxazolidine 
• 144899-51-4 (S)-3-acryloyl-4-benzyl-2,2,5,5-tetramethyloxazolidine 

Relevant articles and documents

Synthesis of tertiary β-hydroxy amides by enolate additions to acylsilanes

The synthesis of tertiary β-hydroxy amides from acylsilanes, acetamides, and electrophiles is described. The addition of amide enolates to acylsilanes generates β-silyloxy homoenolate reactivity by undergoing a 1,2-Brook rearrangement. These unique nucleo

Amide enolate additions to acylsilanes: In situ generation of unusual and stereoselective homoenolate equivalents

The synthesis of β-hydroxy carbonyl compounds is an important goal due to their prevalence in bioactive molecules. A novel approach to construct these structural motifs involves the multicomponent reaction of acylsilanes, amides, and electrophiles. The ad

Effective enantiocontrol in conjugate additions of organocuprates. Highly selective 1,5-chiral induction in the conjugate additions of cuprates to α,β-unsaturated amide derivatives of 2,2-dimethyloxazolidine chiral auxiliaries

α,β-Unsaturated amide derivatives of 2,2-dimethyloxazolidines, developed as new chirality-controlling auxiliaries based on the restricted rotation of the amide linkage, have been applied to the enantiocontrol of conjugate additions of lithium and magnesium cuprates. High selectivities of 1,5-chiral inductions are attained, indicating their promising synthetic potential in asymmetric synthesis. The diastereofacial selectivities depend upon the efficiency of steric shielding by the 4-substituent of the chiral auxiliary, and the reaction of (S)-4-benzyl-3-[(E)-2-butenoyl]-2,2,5,5-tetramethyloxazolidine with Ph2CuMgBrMgBrl is exclusively lk-1,5-inductive. Use of organolithium and organomagnesium show opposite low selectivities. It is concluded that the stereochemistry of cuprate conjugate addition is determined at the step of formation of the d,π* type charge transfer complexes.

New chiral auxiliaries based on conformation control, a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral 2,2-dialkyloxazolidines. Synthesis and conformational analysis of acrylamide derivatives

New chirality-controlling auxiliaries, a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral 2,2-dialkyloxazolidines, are readily prepared from a C2-symmetric 1,2-ethanediamine and naturally occurring α-amino acids, respectively. Con