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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)5265-5267
Number of pages3
JournalChemical Communications
Volume48
Issue number43
DOIs
Publication statusPublished - 2012

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Thymidine Monophosphate
Hexane
Toluene
Sodium
Hexanes
Temperature
N-Boc-pyrrolidine
phenyllithium
pyrrolidine

Keywords

  • zincation
  • N-Boc pyrrolidine
  • solvent dependency

Cite this

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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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Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency. / Garden, Jennifer A.; Kennedy, Alan R.; Mulvey, Robert E.; Robertson, Stuart D.

In: Chemical Communications, Vol. 48, No. 43, 2012, p. 5265-5267.

Research output: Contribution to journalArticle

TY - JOUR

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

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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

M3 - Article

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SP - 5265

EP - 5267

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

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