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Sequential catalytic isomerization and allylic substitution. Conversion of racemic branched allylic carbonates to enantioenriched allylic substitution products.
J Am Chem Soc. 2006 Sep 13; 128(36):11770-1.JA

Abstract

A catalytic protocol for the conversion of readily accessible racemic, branched aromatic allylic esters to branched allylic amines, ethers, and alkyls has been developed. Palladium-catalyzed isomerization of branched allylic esters to terminal allylic esters, followed by sequential iridium-catalyzed allylic substitution, gave the branched allylic products in good yield with high regioisomeric and enantiomeric selectivity. Both electron-rich and electron-poor branched allylic esters gave products in >90% ee. High enantiomeric excesses were also observed for the products from the reactions of 2-thienyl acetates and dienyl carbonates.

Authors+Show Affiliations

Shekhar S
Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.
Trantow B
No affiliation info available
Leitner A
No affiliation info available
Hartwig JF
No affiliation info available

MeSH

Allyl CompoundsCarbonatesCarboxylic AcidsCatalysisIridiumPalladiumStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16953612

Citation

Shekhar, Shashank, et al. "Sequential Catalytic Isomerization and Allylic Substitution. Conversion of Racemic Branched Allylic Carbonates to Enantioenriched Allylic Substitution Products." Journal of the American Chemical Society, vol. 128, no. 36, 2006, pp. 11770-1.
Shekhar S, Trantow B, Leitner A, et al. Sequential catalytic isomerization and allylic substitution. Conversion of racemic branched allylic carbonates to enantioenriched allylic substitution products. J Am Chem Soc. 2006;128(36):11770-1.
Shekhar, S., Trantow, B., Leitner, A., & Hartwig, J. F. (2006). Sequential catalytic isomerization and allylic substitution. Conversion of racemic branched allylic carbonates to enantioenriched allylic substitution products. Journal of the American Chemical Society, 128(36), 11770-1.
Shekhar S, et al. Sequential Catalytic Isomerization and Allylic Substitution. Conversion of Racemic Branched Allylic Carbonates to Enantioenriched Allylic Substitution Products. J Am Chem Soc. 2006 Sep 13;128(36):11770-1. PubMed PMID: 16953612.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sequential catalytic isomerization and allylic substitution. Conversion of racemic branched allylic carbonates to enantioenriched allylic substitution products. AU - Shekhar,Shashank, AU - Trantow,Brian, AU - Leitner,Andreas, AU - Hartwig,John F, PY - 2006/9/7/pubmed PY - 2007/8/19/medline PY - 2006/9/7/entrez SP - 11770 EP - 1 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 36 N2 - A catalytic protocol for the conversion of readily accessible racemic, branched aromatic allylic esters to branched allylic amines, ethers, and alkyls has been developed. Palladium-catalyzed isomerization of branched allylic esters to terminal allylic esters, followed by sequential iridium-catalyzed allylic substitution, gave the branched allylic products in good yield with high regioisomeric and enantiomeric selectivity. Both electron-rich and electron-poor branched allylic esters gave products in >90% ee. High enantiomeric excesses were also observed for the products from the reactions of 2-thienyl acetates and dienyl carbonates. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16953612/Sequential_catalytic_isomerization_and_allylic_substitution__Conversion_of_racemic_branched_allylic_carbonates_to_enantioenriched_allylic_substitution_products_ L2 - https://doi.org/10.1021/ja0644273 DB - PRIME DP - Unbound Medicine ER -