Effect of solvent and lithiating agent on stereoselectivity in lithiation of chiral 1,1'-bis(oxazolinyl)ferrocenes

Jaiwook Park; Sunwoo Lee; Kyo Han Ahn; Chang Woo Cho

doi:10.1016/0040-4039(96)01331-7

Effect of solvent and lithiating agent on stereoselectivity in lithiation of chiral 1,1'-bis(oxazolinyl)ferrocenes

Jaiwook Park, Sunwoo Lee, Kyo Han Ahn, Chang Woo Cho

Pohang University of Science and Technology

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

42 Scopus citations

Abstract

The analysis of phosphorylation products was carried out to investigate the stereoselectivity change in lithiation of 1,1'-bis[(S)-2-(4-R-oxazolinyl)]ferrocene (1) with varying reaction conditions such as solvents, lithiating agents, and temperature. Monolithiation with butyllithiums in Et₂O led to the configuration corresponding to (R)-2, while use of THF favors (S)-2. Dilithiation with sec-BuLi or t-BuLi in Et₂O led to the configuration corresponding to (R,S)-3. However, the step-by-step lithiation at different temperatures with sec-BuLi in Et₂O provided the dilithiated species corresponding to (R,R)-3. sec-BuLi in THF was special to give (S,S)-3 as the major product.

Original language	English
Pages (from-to)	6137-6140
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	34
DOIs	https://doi.org/10.1016/0040-4039(96)01331-7
State	Published - 19 Aug 1996

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title = "Effect of solvent and lithiating agent on stereoselectivity in lithiation of chiral 1,1'-bis(oxazolinyl)ferrocenes",

abstract = "The analysis of phosphorylation products was carried out to investigate the stereoselectivity change in lithiation of 1,1'-bis[(S)-2-(4-R-oxazolinyl)]ferrocene (1) with varying reaction conditions such as solvents, lithiating agents, and temperature. Monolithiation with butyllithiums in Et2O led to the configuration corresponding to (R)-2, while use of THF favors (S)-2. Dilithiation with sec-BuLi or t-BuLi in Et2O led to the configuration corresponding to (R,S)-3. However, the step-by-step lithiation at different temperatures with sec-BuLi in Et2O provided the dilithiated species corresponding to (R,R)-3. sec-BuLi in THF was special to give (S,S)-3 as the major product.",

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T1 - Effect of solvent and lithiating agent on stereoselectivity in lithiation of chiral 1,1'-bis(oxazolinyl)ferrocenes

AU - Park, Jaiwook

AU - Lee, Sunwoo

AU - Ahn, Kyo Han

AU - Cho, Chang Woo

PY - 1996/8/19

Y1 - 1996/8/19

N2 - The analysis of phosphorylation products was carried out to investigate the stereoselectivity change in lithiation of 1,1'-bis[(S)-2-(4-R-oxazolinyl)]ferrocene (1) with varying reaction conditions such as solvents, lithiating agents, and temperature. Monolithiation with butyllithiums in Et2O led to the configuration corresponding to (R)-2, while use of THF favors (S)-2. Dilithiation with sec-BuLi or t-BuLi in Et2O led to the configuration corresponding to (R,S)-3. However, the step-by-step lithiation at different temperatures with sec-BuLi in Et2O provided the dilithiated species corresponding to (R,R)-3. sec-BuLi in THF was special to give (S,S)-3 as the major product.

AB - The analysis of phosphorylation products was carried out to investigate the stereoselectivity change in lithiation of 1,1'-bis[(S)-2-(4-R-oxazolinyl)]ferrocene (1) with varying reaction conditions such as solvents, lithiating agents, and temperature. Monolithiation with butyllithiums in Et2O led to the configuration corresponding to (R)-2, while use of THF favors (S)-2. Dilithiation with sec-BuLi or t-BuLi in Et2O led to the configuration corresponding to (R,S)-3. However, the step-by-step lithiation at different temperatures with sec-BuLi in Et2O provided the dilithiated species corresponding to (R,R)-3. sec-BuLi in THF was special to give (S,S)-3 as the major product.

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U2 - 10.1016/0040-4039(96)01331-7

DO - 10.1016/0040-4039(96)01331-7

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AN - SCOPUS:0030593610

SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

Effect of solvent and lithiating agent on stereoselectivity in lithiation of chiral 1,1'-bis(oxazolinyl)ferrocenes

Abstract

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