Azabicyclic Urethane Rearrangements. I. A Novel Route to Substituted Azabicyclo[3.2.1]oct-2-enes.

Krow, Grant R.; Rodebaugh, Ronald K.; Hyndman, C.; Carmosin, R. J.; DeVicaris, G.

doi:10.1016/s0040-4039(01)87588-2

Cited by 8 publications

(2 citation statements)

References 12 publications

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“…Acetal 25 was then submitted to Hosomi−Sakurai reaction conditions , to yield the allylated product 26 as a single diastereomer. The allylation proceeded with complete exo -selectivity, as indicated by the absence of coupling between H-7 and H-1 in 26 . Carbamate 26 was sensitive to the Lewis acid (BF 3 ·OEt 2 ) at temperatures above −20 °C, so careful control of the reaction temperature and optimization of the isolation procedure were critical to the success of the reaction.…”

Section: Resultsmentioning

confidence: 99%

Development of the [3 + 2] Annulations of Cyclohexenylsilanes and Chlorosulfonyl Isocyanate: Application to the Total Synthesis of (±)-Peduncularine

Roberson

Woerpel

2002

J. Am. Chem. Soc.

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Section: Resultsmentioning

confidence: 99%

Development of the [3 + 2] Annulations of Cyclohexenylsilanes and Chlorosulfonyl Isocyanate: Application to the Total Synthesis of (±)-Peduncularine

Roberson

Woerpel

2002

J. Am. Chem. Soc.

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“…Although plausible, this argument fails t o account for failure of the remaining exo-trichloromethyl isomer to oxymercurate. 16 thanes of secondary amines; however, the urethane of a primary allylic amine 17 afforded N-carbethoxy-3-aminocyclohexanone (18), also in a regiospecific manner.…”

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confidence: 99%

Regioselective functionalization in the oxymercuration of .beta..gamma.-unsaturated urethanes. Synthesis of .gamma.-ketourethanes

Krow¹,

FAN²

1974

J. Org. Chem.

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A specific directing effect on the regiochemistry of oxymercuration has been exerted by a proximate urethane functionality during the oxymercuration of selected 0,y-unsaturated urethanes. This effect has been utilized in the synthesis of y-ketourethanes by reduction of initially formed oxymercurials with sodium borohydride followed by chromic acid oxidation, A mixture of products arising from spontaneous demercuration of an allylic mercurial has been obtained following oxymercuration of a dienic urethane.The oxymercuration reaction, combined with in situ reduction of the oxymercuric intermediate, provides a convenient mild method to achieve Markovnikov hydration of a carbon-carbon double bond.1 Additionally, for those cases where the rules of Markovnikov addition are not applicable, the synthetic utility of oxymercuration is often enhanced by the ability of proximate Lewis base groups to exert specific directing effects in promoting regioselective additions2 We here report a study of the utilization of such a directing effect in the synthesis of cyclic and bicyclic yketourethanes from &-punsaturated urethanes. Involved is a synthetic sequence of regioselective mercuric nitrate oxymercuration, sodium borohydride demercuration, and chromic acid oxidation.3 Hereafter, the sequence of reactions will be referred to as ketofunctionalization.

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ChemInform Abstract: AZABICYCLIC URETHANE REARRANGEMENTS PART 1, A NOVEL ROUTE TO SUBSTITUTED AZABICYCLO(3,2,1)OCT‐2‐ENES

Krow¹,

Rodebaugh²,

Hyndman³

et al. 1973

Chemischer Informationsdienst

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Azabicyclic Urethane Rearrangements. I. A Novel Route to Substituted Azabicyclo[3.2.1]oct-2-enes.

Cited by 8 publications

References 12 publications

Development of the [3 + 2] Annulations of Cyclohexenylsilanes and Chlorosulfonyl Isocyanate: Application to the Total Synthesis of (±)-Peduncularine

Development of the [3 + 2] Annulations of Cyclohexenylsilanes and Chlorosulfonyl Isocyanate: Application to the Total Synthesis of (±)-Peduncularine

Regioselective functionalization in the oxymercuration of .beta..gamma.-unsaturated urethanes. Synthesis of .gamma.-ketourethanes

ChemInform Abstract: AZABICYCLIC URETHANE REARRANGEMENTS PART 1, A NOVEL ROUTE TO SUBSTITUTED AZABICYCLO(3,2,1)OCT‐2‐ENES

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