+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ PDF Full Text
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Translate
+ Recently Requested

Radical cyclization of α-bromo aluminum acetals onto alkenes and alkynes (radic[Al] process): a simple access to γ-lactols and 4-methylene-γ-lactols

Radical cyclization of α-bromo aluminum acetals onto alkenes and alkynes (radic[Al] process): a simple access to γ-lactols and 4-methylene-γ-lactols

Chemistry 17(20): 5613-5627

An efficient preparation of γ-lactols and methylene-γ-lactols is described. Highly acid-sensitive lactols are prepared in a concise manner by using a radical cyclization of aluminum acetals. The precursors for the radical reactions are readily prepared from allyl or propargyl alcohols and α-bromo acids. Functionalization of the resulting γ-lactols and methylene-γ-lactols can be achieved following isolation, leading to synthetically useful building blocks, such as 1,4-diols, 1,4-dienes, γ-lactones, and polysubstituted tetrahydrofurans.

(PDF emailed within 0-6 h: $19.90)

Accession: 055345752

Download citation: RISBibTeXText

PMID: 21472805

DOI: 10.1002/chem.201100049

Related references

Radical cyclization of alpha-bromo aluminum acetals: an easy approach to gamma-lactols. Angewandte Chemie 48(50): 9549-9552, 2009

Iodocyclization of unsaturated lactols and acetals a new route to furo 2 3 b furans and pyrans. Tetrahedron Letters 27(4): 497-500, 1986

Synthesis of Polysubstituted γ-Butenolides via a Radical Pathway: Cyclization of α-Bromo Aluminium Acetals and Comparison with the Cyclization of α-Bromoesters at High Temperature. Chemistry 21(32): 11378-11386, 2015

An organocatalytic Michael-cyclization cascade of 4-oxa-α,β-unsaturated carboxylic acids with aldehydes: facile synthesis of chiral γ-lactols and trisubstituted γ-lactones. Chemical Communications 51(17): 3596-3599, 2015

Indium(I) iodide as a radical initiator: intramolecular cyclization of functionalized bromo-alkynes to substituted tetrahydrofurans. Tetrahedron Letters 47(17): 2859-2861, 2006

Intermolecular Visible-Light Photoredox Atom-Transfer Radical [3+2]-Cyclization of 2-(Iodomethyl)cyclopropane-1,1-dicarboxylate with Alkenes and Alkynes. Chemistry 19(36): 11878-11882, 2013

Synthesis of New Bicycloalkane Derivatives from Allylic Alcohols/Lactols by a Tandem Isomerization-Intramolecular Aldolization Process. Synlett 2009(12): 1969-1973, 2009

Lactols in an asymmetric aldol-desymmetrization sequence: access to tetrahydro-4H-furo[2,3-b]pyran-2-one and tetrahydro-4H-furo[2,3-b]furan-2-one derivatives. Organic & Biomolecular Chemistry 15(6): 1407-1417, 2017

Sesquiterpene lactols from laserpitium halleri. Phytochemistry (Oxford) 26(6): 1755-1758, 1987

Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition-cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of cyclic beta-amino acids. Tetrahedron 58(22): 4459-4479, 2002

Carboxyethyl Homologation of Lactols: Synthons For Dinorprostanoids. Synthetic Communications 18(18): 2233-2240, 1988

Synthetic methods towards substituted lactam lactols. Abstracts of Papers American Chemical Society 226(1-2): ORGN 379, 2003

Titanocene-Catalyzed Reduction of Lactones to Lactols. Journal of Organic Chemistry 62(24): 8522-8528, 2001

Lactols derived from steroidal 17a-oxa-D-homo lactones. Journal of Organic Chemistry 30(10): 3564-3566, 1965

Reduction of gamma bromo alpha acetylenic acetals by chromous salts access to acetals and alpha allenic aldehydes. Tetrahedron Letters 26(1): 51-52, 1985