Reversal of regioselection in the rearrangement of cinnamate diol cyclic iminocarbonates

Gae Y. Cho; Jung Nam Park; Soo Y. Ko

doi:10.1016/S0040-4039(00)00017-4

Reversal of regioselection in the rearrangement of cinnamate diol cyclic iminocarbonates

Gae Y. Cho, Jung Nam Park, Soo Y. Ko

Department of Chemistry & Nanoscience

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

6 Scopus citations

Abstract

The rearrangement of cinnamate diol cyclic iminocarbonates can be regioselectively controlled by using, as the nucleophile, Bu₄NBr (for β[benzylic]-nitrogen regioselection) or LiI (for the α-nitrogen isomers). This discovery will expand the synthetic utilities of the cyclic iminocarbonate rearrangement and the asymmetric dihydroxylation processes. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	1789-1792
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(00)00017-4
State	Published - 11 Mar 2000

Bibliographical note

Funding Information:
This work was supported by the MOST through the National R&D Program for Women’s Universities (Project No. N6-01-01-A-08), and by the KOSEF through the Center for Cell Signaling Research at Ewha Womans University.

Keywords

Asymmetric dihydroxylation
Cyclic iminocarbonate rearrangement
Regioselection

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10.1016/S0040-4039(00)00017-4

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title = "Reversal of regioselection in the rearrangement of cinnamate diol cyclic iminocarbonates",

abstract = "The rearrangement of cinnamate diol cyclic iminocarbonates can be regioselectively controlled by using, as the nucleophile, Bu4NBr (for β[benzylic]-nitrogen regioselection) or LiI (for the α-nitrogen isomers). This discovery will expand the synthetic utilities of the cyclic iminocarbonate rearrangement and the asymmetric dihydroxylation processes. (C) 2000 Elsevier Science Ltd.",

keywords = "Asymmetric dihydroxylation, Cyclic iminocarbonate rearrangement, Regioselection",

author = "Cho, \{Gae Y.\} and Park, \{Jung Nam\} and Ko, \{Soo Y.\}",

note = "Funding Information: This work was supported by the MOST through the National R\&D Program for Women{\textquoteright}s Universities (Project No. N6-01-01-A-08), and by the KOSEF through the Center for Cell Signaling Research at Ewha Womans University. ",

year = "2000",

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doi = "10.1016/S0040-4039(00)00017-4",

language = "English",

volume = "41",

pages = "1789--1792",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Reversal of regioselection in the rearrangement of cinnamate diol cyclic iminocarbonates

AU - Cho, Gae Y.

AU - Park, Jung Nam

AU - Ko, Soo Y.

N1 - Funding Information: This work was supported by the MOST through the National R&D Program for Women’s Universities (Project No. N6-01-01-A-08), and by the KOSEF through the Center for Cell Signaling Research at Ewha Womans University.

PY - 2000/3/11

Y1 - 2000/3/11

N2 - The rearrangement of cinnamate diol cyclic iminocarbonates can be regioselectively controlled by using, as the nucleophile, Bu4NBr (for β[benzylic]-nitrogen regioselection) or LiI (for the α-nitrogen isomers). This discovery will expand the synthetic utilities of the cyclic iminocarbonate rearrangement and the asymmetric dihydroxylation processes. (C) 2000 Elsevier Science Ltd.

AB - The rearrangement of cinnamate diol cyclic iminocarbonates can be regioselectively controlled by using, as the nucleophile, Bu4NBr (for β[benzylic]-nitrogen regioselection) or LiI (for the α-nitrogen isomers). This discovery will expand the synthetic utilities of the cyclic iminocarbonate rearrangement and the asymmetric dihydroxylation processes. (C) 2000 Elsevier Science Ltd.

KW - Asymmetric dihydroxylation

KW - Cyclic iminocarbonate rearrangement

KW - Regioselection

UR - https://www.scopus.com/pages/publications/0342906193

U2 - 10.1016/S0040-4039(00)00017-4

DO - 10.1016/S0040-4039(00)00017-4

M3 - Article

AN - SCOPUS:0342906193

SN - 0040-4039

VL - 41

SP - 1789

EP - 1792

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Reversal of regioselection in the rearrangement of cinnamate diol cyclic iminocarbonates

Abstract

Bibliographical note

Keywords

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