Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency

Jennifer A. Garden; Alan R. Kennedy; Robert E. Mulvey; Stuart D. Robertson

doi:10.1039/c2cc31793a

Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency

Jennifer A. Garden, Alan R. Kennedy, Robert E. Mulvey, Stuart D. Robertson

Pure And Applied Chemistry

Research output: Contribution to journal › Article

12 Citations (Scopus)

Abstract

Sodium TMP-zincate, [(TMEDA)Na(TMP)(Bu-t)Zn(Bu-t)], can deproto-zincate N-Boc pyrrolidine at ambient temperature in hexane solution, whereas in toluene the captured alpha-carbanion of the heterocycle attacks the solvent setting off a cascade of reactions that ultimately produce a pyrrolidine-substituted enolate.

Original language	English
Pages (from-to)	5265-5267
Number of pages	3
Journal	Chemical Communications
Volume	48
Issue number	43
DOIs	https://doi.org/10.1039/c2cc31793a
Publication status	Published - 2012

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Keywords

zincation
N-Boc pyrrolidine
solvent dependency

Cite this

Garden, J. A., Kennedy, A. R., Mulvey, R. E., & Robertson, S. D. (2012). Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency. Chemical Communications, 48(43), 5265-5267. https://doi.org/10.1039/c2cc31793a

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title = "Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency",

abstract = "Sodium TMP-zincate, [(TMEDA)Na(TMP)(Bu-t)Zn(Bu-t)], can deproto-zincate N-Boc pyrrolidine at ambient temperature in hexane solution, whereas in toluene the captured alpha-carbanion of the heterocycle attacks the solvent setting off a cascade of reactions that ultimately produce a pyrrolidine-substituted enolate.",

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author = "Garden, {Jennifer A.} and Kennedy, {Alan R.} and Mulvey, {Robert E.} and Robertson, {Stuart D.}",

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T1 - Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency

AU - Garden, Jennifer A.

AU - Kennedy, Alan R.

AU - Mulvey, Robert E.

AU - Robertson, Stuart D.

PY - 2012

Y1 - 2012

N2 - Sodium TMP-zincate, [(TMEDA)Na(TMP)(Bu-t)Zn(Bu-t)], can deproto-zincate N-Boc pyrrolidine at ambient temperature in hexane solution, whereas in toluene the captured alpha-carbanion of the heterocycle attacks the solvent setting off a cascade of reactions that ultimately produce a pyrrolidine-substituted enolate.

AB - Sodium TMP-zincate, [(TMEDA)Na(TMP)(Bu-t)Zn(Bu-t)], can deproto-zincate N-Boc pyrrolidine at ambient temperature in hexane solution, whereas in toluene the captured alpha-carbanion of the heterocycle attacks the solvent setting off a cascade of reactions that ultimately produce a pyrrolidine-substituted enolate.

KW - zincation

KW - N-Boc pyrrolidine

KW - solvent dependency

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DO - 10.1039/c2cc31793a

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JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

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10.1039/c2cc31793a

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Projects

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

Project: Research

EXPLOITING SYNTHETIC AND STRUCTURAL SYNERGISM IN ALKALI-METAL-MEDIATED ORGANOTRANSITIONMETALLATION (AMMO)

Project: Research

Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency

Abstract

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Keywords

Cite this

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Projects

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

EXPLOITING SYNTHETIC AND STRUCTURAL SYNERGISM IN ALKALI-METAL-MEDIATED ORGANOTRANSITIONMETALLATION (AMMO)