Practical synthesis of ynolate anions: Naphthalene-catalyzed reductive lithiation of α,α-dibromo esters

Mitsuru Shindo; Ryoko Koretsune; Wakako Yokota; Kotaro Itoh; Kozo Shishido

doi:10.1016/S0040-4039(01)01799-3

Practical synthesis of ynolate anions: Naphthalene-catalyzed reductive lithiation of α,α-dibromo esters

Mitsuru Shindo, Ryoko Koretsune, Wakako Yokota, Kotaro Itoh, Kozo Shishido

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

13 Citations (Scopus)

Abstract

Reductive lithiation of α,α-dibromo esters using lithium naphthalenide afforded ester dianions leading to ynolate anions in good yields. Naphthalene-catalyzed reductive lithiation was also accomplished. This is a convenient, economical and practical method for the preparation of ynolate anions.

Original language	English
Pages (from-to)	8357-8360
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	47
DOIs	https://doi.org/10.1016/S0040-4039(01)01799-3
Publication status	Published - Nov 19 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)01799-3

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title = "Practical synthesis of ynolate anions: Naphthalene-catalyzed reductive lithiation of α,α-dibromo esters",

abstract = "Reductive lithiation of α,α-dibromo esters using lithium naphthalenide afforded ester dianions leading to ynolate anions in good yields. Naphthalene-catalyzed reductive lithiation was also accomplished. This is a convenient, economical and practical method for the preparation of ynolate anions.",

author = "Mitsuru Shindo and Ryoko Koretsune and Wakako Yokota and Kotaro Itoh and Kozo Shishido",

note = "Funding Information: This research was partially supported by a Grant in Aid for Scientific Research on Priority Areas (A) {\textquoteleft}Exploitation of Multi-Element Cyclic Molecules{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and the Asahi Glass Foundation.",

year = "2001",

month = nov,

day = "19",

doi = "10.1016/S0040-4039(01)01799-3",

language = "English",

volume = "42",

pages = "8357--8360",

journal = "Tetrahedron Letters",

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T1 - Practical synthesis of ynolate anions

T2 - Naphthalene-catalyzed reductive lithiation of α,α-dibromo esters

AU - Shindo, Mitsuru

AU - Koretsune, Ryoko

AU - Yokota, Wakako

AU - Itoh, Kotaro

AU - Shishido, Kozo

N1 - Funding Information: This research was partially supported by a Grant in Aid for Scientific Research on Priority Areas (A) ‘Exploitation of Multi-Element Cyclic Molecules’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and the Asahi Glass Foundation.

PY - 2001/11/19

Y1 - 2001/11/19

N2 - Reductive lithiation of α,α-dibromo esters using lithium naphthalenide afforded ester dianions leading to ynolate anions in good yields. Naphthalene-catalyzed reductive lithiation was also accomplished. This is a convenient, economical and practical method for the preparation of ynolate anions.

AB - Reductive lithiation of α,α-dibromo esters using lithium naphthalenide afforded ester dianions leading to ynolate anions in good yields. Naphthalene-catalyzed reductive lithiation was also accomplished. This is a convenient, economical and practical method for the preparation of ynolate anions.

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U2 - 10.1016/S0040-4039(01)01799-3

DO - 10.1016/S0040-4039(01)01799-3

M3 - Article

AN - SCOPUS:0035914518

SN - 0040-4039

VL - 42

SP - 8357

EP - 8360

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Practical synthesis of ynolate anions: Naphthalene-catalyzed reductive lithiation of α,α-dibromo esters

Abstract

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