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  • 706671 - (4S,5S)-2-Allyl-2-chloro-3,4-dimethyl-5-phenyl-1-oxa-3-aza-2-silacyclopentane

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706671 Sigma-Aldrich

(4S,5S)-2-Allyl-2-chloro-3,4-dimethyl-5-phenyl-1-oxa-3-aza-2-silacyclopentane

Synonym: (1S,2S)-pseudoephedrine allylchlorosilane, (4S,5S)-2-Allyl-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazasilolidine, (4S,5S)-2-Chloro-3,4-dimethyl-5-phenyl-2-(2-propenyl)-1-oxa-3-aza-2-silacyclopentane

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Properties

Related Categories Allylation, Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents
InChI Key   XHCRAANIMMYPDV-APBZJUGRSA-N
optical activity   [α]20/D 72.5°, c = 0.6 in ethanol (200 proof)
refractive index   n20/D 1.517
bp   120 °C/5 mmHg
density   1.095 g/mL at 25 °C

Description

Application

Reagent used in the enantioselective allylation of aldehydes

Leighton’s Strained Silacycles: Powerful Enantioselective Allylation Reagents

• Practical, enantioselective allylation of acylhydrazones
• Enantioselective allylation of ketimines: synthesis of tertiary carbinamines

General description

This product is a mixture of diastereomers.

Packaging

1 g in glass bottle

Legal Information

U.S. Patent No. 7,534,905

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3132 / PGII
WGK Germany 
3
Flash Point(F) 
100.4 °F
Flash Point(C) 
38 °C
Protocols & Articles

Articles

Chiral Silacycles for Enantioselective Allylation and Crotylation Reactions

The asymmetric allylation and crotylation of aldehydes and other carbonyl compounds remains one of the most fundamental reactions for the construction of chiral building blocks. While numerous method...
Aaron Thornton
Chemfiles Volume 11 Article 1
Keywords: Addition reactions, Asymmetric synthesis, Building blocks, Catalysis, Chiral auxiliaries, Methods, Purification

Leighton’s Chiral Allylation Reagents

The asymmetric allylation of carbonyl compounds remains one of the most important and fundamental addition reactions for the synthesis of optically active chiral building blocks homoallylic alcohols.
Keywords: Addition reactions, Asymmetric synthesis, Building blocks, Medicinal chemistry, Reductions

Related Content

Leighton’s Strained Silacycles: Powerful Enantioselective Allylation Reagents

The asymmetric allylation of carbonyl compounds remains one of the most important and fundamental addition reactions for the synthesis of optically active chiral building blocks. Prof. James L. Leigh...
Keywords: Addition reactions, Aldrichimica Acta, Alkylations, Asymmetric synthesis, Building blocks, Cycloadditions, Friedel-Crafts Alkylation, Medicinal chemistry, Methods, Reductions

Peer-Reviewed Papers
15

References

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