C1-Substituted N-tert-butoxycarbonyl-5-syn-tert-butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexanes as conformationally constrained β-amino acid precursors

Grant R. Krow; Deepa Gandla; Kevin C. Cannon; Chuck W. Ross; Patrick J. Carroll

doi:10.1515/hc-2016-0046

C¹-Substituted N-tert-butoxycarbonyl-5-syn-tert-butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexanes as conformationally constrained β-amino acid precursors

Grant R. Krow, Deepa Gandla, Kevin C. Cannon, Chuck W. Ross, Patrick J. Carroll

Division of Engineering and Science (Abington)

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

1 Scopus citations

Abstract

Regioselective introduction and transformation of substituents at the C¹ carbon of N-tert-butoxycarbonyl-5-syn-tert-butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexane (7) is described. These azabicycles are precursors to conformationally constrained β-amino acids with potential to form oligomers with definite secondary structures. Selected examples of these precursors are converted into their corresponding amino acid derivatives.

Original language	English (US)
Pages (from-to)	319-328
Number of pages	10
Journal	Heterocyclic Communications
Volume	22
Issue number	6
DOIs	https://doi.org/10.1515/hc-2016-0046
State	Published - Dec 1 2016

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "C1-Substituted N-tert-butoxycarbonyl-5-syn-tert-butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexanes as conformationally constrained β-amino acid precursors",

abstract = "Regioselective introduction and transformation of substituents at the C1 carbon of N-tert-butoxycarbonyl-5-syn-tert-butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexane (7) is described. These azabicycles are precursors to conformationally constrained β-amino acids with potential to form oligomers with definite secondary structures. Selected examples of these precursors are converted into their corresponding amino acid derivatives.",

author = "Krow, {Grant R.} and Deepa Gandla and Cannon, {Kevin C.} and Ross, {Chuck W.} and Carroll, {Patrick J.}",

note = "Publisher Copyright: {\textcopyright} 2016 Walter de Gruyter GmbH, Berlin/Boston.",

year = "2016",

month = dec,

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doi = "10.1515/hc-2016-0046",

language = "English (US)",

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T1 - C1-Substituted N-tert-butoxycarbonyl-5-syn-tert-butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexanes as conformationally constrained β-amino acid precursors

AU - Krow, Grant R.

AU - Gandla, Deepa

AU - Cannon, Kevin C.

AU - Ross, Chuck W.

AU - Carroll, Patrick J.

PY - 2016/12/1

Y1 - 2016/12/1

N2 - Regioselective introduction and transformation of substituents at the C1 carbon of N-tert-butoxycarbonyl-5-syn-tert-butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexane (7) is described. These azabicycles are precursors to conformationally constrained β-amino acids with potential to form oligomers with definite secondary structures. Selected examples of these precursors are converted into their corresponding amino acid derivatives.

AB - Regioselective introduction and transformation of substituents at the C1 carbon of N-tert-butoxycarbonyl-5-syn-tert-butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexane (7) is described. These azabicycles are precursors to conformationally constrained β-amino acids with potential to form oligomers with definite secondary structures. Selected examples of these precursors are converted into their corresponding amino acid derivatives.

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EP - 328

JO - Heterocyclic Communications

JF - Heterocyclic Communications

IS - 6

ER -

C¹-Substituted N-tert-butoxycarbonyl-5-syn-tert-butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexanes as conformationally constrained β-amino acid precursors

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