Literature DB >> 20178346

Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy.

Alan Rolfe1, Thiwanka B Samarakoon, Paul R Hanson.   

Abstract

A formal [4+3] epoxide cascade protocol utilizing ambiphilic sulfonamides and a variety of epoxides (masked ambiphiles) has been developed for the generation of benzothiaoxazepine-1,1'-dioxides and oxathiazepine-1,1'-dioxides. This protocol combines an epoxide ring-opening with either an S(N)Ar or oxa-Michael cyclization pathway.

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Year:  2010        PMID： 20178346      PMCID： PMC2864497          DOI： 10.1021/ol100035e

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  26 in total

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6.  Amphoteric amino aldehydes reroute the aza-Michael reaction.

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  23 in total

1.  S(N)Ar-based, facile synthesis of a library of benzothiaoxazepine-1,1'-dioxides.

Authors:  Alan Rolfe; Thiwanka B Samarakoon; Sarra V Klimberg; Marek Brzozowski; Benjamin Neuenswander; Gerald H Lushington; Paul R Hanson
Journal:  J Comb Chem       Date:  2010-09-29

2.  Synthesis of epoxybenzo[d]isothiazole 1,1-dioxides via a reductive-Heck, metathesis-sequestration protocol.

Authors:  Naeem Asad; Paul R Hanson; Toby R Long; Dinesh K Rayabarapu; Alan Rolfe
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3.  Facile (triazolyl)methylation of MACOS-derived benzofused sultams utilizing ROMP-derived OTP reagents.

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5.  Electrophilic aromatic prenylation via cascade cyclization.

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6.  Accessing Stereochemically Rich Sultams via Microwave-Assisted, Continuous Flow Organic Synthesis (MACOS) Scale-out.

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7.  A formal [4 + 4] complementary ambiphile pairing reaction: a new cyclization pathway for ortho-quinone methides.

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8.  Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.

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9.  Rapid, scalable assembly of stereochemically rich, mono- and bicyclic acyl sultams.

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10.  Effective synthesis of chiral N-fluoroaryl aziridines through enantioselective aziridination of alkenes with fluoroaryl azides.

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Journal:  Angew Chem Int Ed Engl       Date:  2013-04-15       Impact factor: 15.336
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