444575-90-0

Basic information

• Product Name: (R)-(+)-tert-butyl 1-phenylprop-2-en-1-yl carbonate
• Synonyms: (R)-(+)-tert-butyl 1-phenylprop-2-en-1-yl carbonate
• CAS NO: 444575-90-0
• Molecular Weight: 234.295
• Mol File: 444575-90-0.mol

Chemical Properties

• CAS DataBase Reference: (R)-(+)-tert-butyl 1-phenylprop-2-en-1-yl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-tert-butyl 1-phenylprop-2-en-1-yl carbonate(444575-90-0)
• EPA Substance Registry System: (R)-(+)-tert-butyl 1-phenylprop-2-en-1-yl carbonate(444575-90-0)

Safety Data

• Hazardous Substances Data: 444575-90-0(Hazardous Substances Data)

Upstream product

• 7651-82-3 isoquinolin-6-ol 
• 444575-79-5 carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 104713-12-4 (R)-1-phenylprop-2-en-1-ol 

Downstream Products

• 1332506-74-7 (2R,1'R)-tert-butyl(dimethyl)(2-(1'-(phenyl)allyloxy)but-3-enyloxy)silane 
• 1332506-70-3 (2S,1'R)-tert-butyl(dimethyl)(2-(1'-(phenyl)allyloxy)but-3-enyloxy)silane 

Relevant articles and documents

Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol

Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.

Time-dependent enantiodivergent synthesis via sequential kinetic resolution

The preparation of both enantiomers of chiral molecules is among the most fundamental tasks in organic synthesis, medicinal chemistry and materials science. Achieving this goal typically requires reversing the absolute configuration of the chiral component employed in the reaction system that is being used. The task becomes challenging when the natural source of the chiral component is not available in both configurations. Herein, we report a time-dependent enantiodivergent synthesis, in which an Ir-catalysed allylic substitution reaction uses one catalyst sequentially to promote two kinetic resolution reactions, enabling the synthesis of both enantiomers of the product using the same enantiomer of a chiral catalyst. The appropriate permutation of individual reaction rates is essential for the isolation of the chiral products in opposite configurations with high enantiopurity when quenched at different reaction times. This work provides an alternative solution for the preparation of both enantiomers of chiral molecules. [Figure not available: see fulltext.].

Synthesis of enantiopure 1-arylprop-2-en-1-ols and their tert-butyl carbonates

(Chemical Equation Presented) Enantiomerically pure 1-arylpropenols 8 have been prepared by resolution of the corresponding racemates, using the lipase formulation Novozyme 435. Deprotonation of the latter alcohols with n-BuLi, followed by derivatization with (t- BuO)2CO, afforded the corresponding carbonates 5. Optimization of the process is presented.