Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold

Roland E. Dolle; Michael C. Barden; Paul E. Brennan; Gulzar Ahmed; Vinh Tran; Douglas M. Ho

doi:10.1016/S0040-4039(99)00391-3

Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold

Roland E. Dolle
, Michael C. Barden
, Paul E. Brennan
, Gulzar Ahmed
, Vinh Tran
, Douglas M. Ho

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

15 Scopus citations

Abstract

Hydrazone 4 undergoes tandem intramolecular Michael addition - intramolecular azomethine imine cyctoaddition in ethanol at reflux to furnish the tricyclic pyrazoline methyl ester 3 in 75% yield. A five-step conversion of 3 to N¹-Alloc-6-(N-Boc-aminomethyl)-1-azaspiro[4.4]nonane-2-acetic acid 1 provides access to a unique tri-functionalized scaffold for combinatorial chemistry.

Original language	English
Pages (from-to)	2907-2908
Number of pages	2
Journal	Tetrahedron Letters
Volume	40
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4039(99)00391-3
State	Published - Apr 9 1999

Keywords

Azomethine imine
Combinatorial chemistry
Intramolecular dipolar cycloaddition

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10.1016/S0040-4039(99)00391-3

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title = "Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold",

abstract = "Hydrazone 4 undergoes tandem intramolecular Michael addition - intramolecular azomethine imine cyctoaddition in ethanol at reflux to furnish the tricyclic pyrazoline methyl ester 3 in 75\% yield. A five-step conversion of 3 to N1-Alloc-6-(N-Boc-aminomethyl)-1-azaspiro[4.4]nonane-2-acetic acid 1 provides access to a unique tri-functionalized scaffold for combinatorial chemistry.",

keywords = "Azomethine imine, Combinatorial chemistry, Intramolecular dipolar cycloaddition",

author = "Dolle, \{Roland E.\} and Barden, \{Michael C.\} and Brennan, \{Paul E.\} and Gulzar Ahmed and Vinh Tran and Ho, \{Douglas M.\}",

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doi = "10.1016/S0040-4039(99)00391-3",

language = "English",

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T1 - Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold

AU - Dolle, Roland E.

AU - Barden, Michael C.

AU - Brennan, Paul E.

AU - Ahmed, Gulzar

AU - Tran, Vinh

AU - Ho, Douglas M.

PY - 1999/4/9

Y1 - 1999/4/9

N2 - Hydrazone 4 undergoes tandem intramolecular Michael addition - intramolecular azomethine imine cyctoaddition in ethanol at reflux to furnish the tricyclic pyrazoline methyl ester 3 in 75% yield. A five-step conversion of 3 to N1-Alloc-6-(N-Boc-aminomethyl)-1-azaspiro[4.4]nonane-2-acetic acid 1 provides access to a unique tri-functionalized scaffold for combinatorial chemistry.

AB - Hydrazone 4 undergoes tandem intramolecular Michael addition - intramolecular azomethine imine cyctoaddition in ethanol at reflux to furnish the tricyclic pyrazoline methyl ester 3 in 75% yield. A five-step conversion of 3 to N1-Alloc-6-(N-Boc-aminomethyl)-1-azaspiro[4.4]nonane-2-acetic acid 1 provides access to a unique tri-functionalized scaffold for combinatorial chemistry.

KW - Azomethine imine

KW - Combinatorial chemistry

KW - Intramolecular dipolar cycloaddition

UR - https://www.scopus.com/pages/publications/0033537907

U2 - 10.1016/S0040-4039(99)00391-3

DO - 10.1016/S0040-4039(99)00391-3

M3 - Article

AN - SCOPUS:0033537907

SN - 0040-4039

VL - 40

SP - 2907

EP - 2908

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold

Abstract

Keywords

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