An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application

Fengtian Xue; Richard B. Silverman

doi:10.1016/j.tetlet.2010.03.009

An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application

Fengtian Xue, Richard B. Silverman^*

^*Corresponding author for this work

Chemistry

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

8 Scopus citations

Abstract

We report a fast N→O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hyd roxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state.

Original language	English (US)
Pages (from-to)	2536-2538
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2010.03.009
State	Published - May 5 2010

Keywords

Boc group migration
Cross-over experiment
Intramolecular migration
N to O migration

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.03.009

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title = "An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application",

abstract = "We report a fast N→O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hyd roxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state.",

keywords = "Boc group migration, Cross-over experiment, Intramolecular migration, N to O migration",

author = "Fengtian Xue and Silverman, {Richard B.}",

note = "Funding Information: The authors are grateful for financial support from the National Institutes of Health ( GM049725 ).",

year = "2010",

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doi = "10.1016/j.tetlet.2010.03.009",

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TY - JOUR

T1 - An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application

AU - Xue, Fengtian

AU - Silverman, Richard B.

N1 - Funding Information: The authors are grateful for financial support from the National Institutes of Health ( GM049725 ).

PY - 2010/5/5

Y1 - 2010/5/5

N2 - We report a fast N→O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hyd roxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state.

AB - We report a fast N→O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hyd roxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state.

KW - Boc group migration

KW - Cross-over experiment

KW - Intramolecular migration

KW - N to O migration

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DO - 10.1016/j.tetlet.2010.03.009

M3 - Article

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AN - SCOPUS:77950296482

SN - 0040-4039

VL - 51

SP - 2536

EP - 2538

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application

Abstract

Keywords

ASJC Scopus subject areas

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