Enantioselective intramolecular aldehyde α-alkylation with simple olefins: Direct access to homo-ene products

Robert J. Comito; Fernanda G. Finelli; David W.C. Macmillan

doi:10.1021/ja4047312

Enantioselective intramolecular aldehyde α-alkylation with simple olefins: Direct access to homo-ene products

Robert J. Comito, Fernanda G. Finelli, David W.C. Macmillan

Research output: Contribution to journal › Article › peer-review

72 Scopus citations

Abstract

A highly selective method for the synthesis of asymmetrically substituted carbocycles and heterocycles from unactivated aldehyde-olefin precursors has been achieved via enantioselective SOMO-catalysis. Addition of a catalytically generated enamine radical cation across a pendent olefin serves to establish a general asymmetric strategy toward the production of a wide range of formyl-substituted rings with alkene transposition. Conceptually, this novel mechanism allows direct access to "homo-ene"-type products.

Original language	English (US)
Pages (from-to)	9358-9361
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	25
DOIs	https://doi.org/10.1021/ja4047312
State	Published - Jun 26 2013

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja4047312

Cite this

@article{780fa44ad8fb471f95d82ddc38fbc77f,

title = "Enantioselective intramolecular aldehyde α-alkylation with simple olefins: Direct access to homo-ene products",

abstract = "A highly selective method for the synthesis of asymmetrically substituted carbocycles and heterocycles from unactivated aldehyde-olefin precursors has been achieved via enantioselective SOMO-catalysis. Addition of a catalytically generated enamine radical cation across a pendent olefin serves to establish a general asymmetric strategy toward the production of a wide range of formyl-substituted rings with alkene transposition. Conceptually, this novel mechanism allows direct access to {"}homo-ene{"}-type products.",

author = "Comito, {Robert J.} and Finelli, {Fernanda G.} and Macmillan, {David W.C.}",

year = "2013",

month = jun,

day = "26",

doi = "10.1021/ja4047312",

language = "English (US)",

volume = "135",

pages = "9358--9361",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "25",

}

TY - JOUR

T1 - Enantioselective intramolecular aldehyde α-alkylation with simple olefins

T2 - Direct access to homo-ene products

AU - Comito, Robert J.

AU - Finelli, Fernanda G.

AU - Macmillan, David W.C.

PY - 2013/6/26

Y1 - 2013/6/26

N2 - A highly selective method for the synthesis of asymmetrically substituted carbocycles and heterocycles from unactivated aldehyde-olefin precursors has been achieved via enantioselective SOMO-catalysis. Addition of a catalytically generated enamine radical cation across a pendent olefin serves to establish a general asymmetric strategy toward the production of a wide range of formyl-substituted rings with alkene transposition. Conceptually, this novel mechanism allows direct access to "homo-ene"-type products.

AB - A highly selective method for the synthesis of asymmetrically substituted carbocycles and heterocycles from unactivated aldehyde-olefin precursors has been achieved via enantioselective SOMO-catalysis. Addition of a catalytically generated enamine radical cation across a pendent olefin serves to establish a general asymmetric strategy toward the production of a wide range of formyl-substituted rings with alkene transposition. Conceptually, this novel mechanism allows direct access to "homo-ene"-type products.

UR - http://www.scopus.com/inward/record.url?scp=84879542001&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84879542001&partnerID=8YFLogxK

U2 - 10.1021/ja4047312

DO - 10.1021/ja4047312

M3 - Article

C2 - 23745728

AN - SCOPUS:84879542001

SN - 0002-7863

VL - 135

SP - 9358

EP - 9361

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 25

ER -

Enantioselective intramolecular aldehyde α-alkylation with simple olefins: Direct access to homo-ene products

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this