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 › peer-review

17 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

Keywords

zincation
N-Boc pyrrolidine
solvent dependency

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10.1039/c2cc31793a

Cite this

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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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journal = "Chemical Communications",

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AU - Kennedy, Alan R.

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AU - Robertson, Stuart D.

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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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U2 - 10.1039/c2cc31793a

DO - 10.1039/c2cc31793a

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SN - 1359-7345

VL - 48

SP - 5265

EP - 5267

JO - Chemical Communications

JF - Chemical Communications

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ER -

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

Abstract

Keywords

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

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

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

Abstract

Keywords

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

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

Cite this