Enantioselective reactions of α-methoxybenzyllithium generated by t-BuLi/chiral bis(oxazoline) complex with aldehydes

Katsuhiko Tomooka; Lan Fang Wang; Nobuyuki Komine; Takeshi Nakai

doi:10.1016/S0040-4039(99)01365-9

Enantioselective reactions of α-methoxybenzyllithium generated by t-BuLi/chiral bis(oxazoline) complex with aldehydes

Katsuhiko Tomooka, Lan Fang Wang, Nobuyuki Komine, Takeshi Nakai

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

39 Citations (Scopus)

Abstract

The title reaction is shown to afford the corresponding 1,2-diol monomethyl ethers in moderate-to-high levels of % ee (up to 98%) and % de (up to 90% anti), depending markedly on the aldehyde reactivity. The origin of the enantioselectivity is discussed in terms of a dynamic thermodynamic resolution mechanism.

Original language	English
Pages (from-to)	6813-6816
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4039(99)01365-9
Publication status	Published - Sept 10 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)01365-9

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title = "Enantioselective reactions of α-methoxybenzyllithium generated by t-BuLi/chiral bis(oxazoline) complex with aldehydes",

abstract = "The title reaction is shown to afford the corresponding 1,2-diol monomethyl ethers in moderate-to-high levels of % ee (up to 98%) and % de (up to 90% anti), depending markedly on the aldehyde reactivity. The origin of the enantioselectivity is discussed in terms of a dynamic thermodynamic resolution mechanism.",

author = "Katsuhiko Tomooka and Wang, {Lan Fang} and Nobuyuki Komine and Takeshi Nakai",

note = "Funding Information: This work was supportebdy a Grant-in-Aidfo r ScientificR esearchfr omthe Ministry of Education and theJ SPS Researchfo r theF utureP rogram.",

year = "1999",

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doi = "10.1016/S0040-4039(99)01365-9",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Enantioselective reactions of α-methoxybenzyllithium generated by t-BuLi/chiral bis(oxazoline) complex with aldehydes

AU - Tomooka, Katsuhiko

AU - Wang, Lan Fang

AU - Komine, Nobuyuki

AU - Nakai, Takeshi

N1 - Funding Information: This work was supportebdy a Grant-in-Aidfo r ScientificR esearchfr omthe Ministry of Education and theJ SPS Researchfo r theF utureP rogram.

PY - 1999/9/10

Y1 - 1999/9/10

N2 - The title reaction is shown to afford the corresponding 1,2-diol monomethyl ethers in moderate-to-high levels of % ee (up to 98%) and % de (up to 90% anti), depending markedly on the aldehyde reactivity. The origin of the enantioselectivity is discussed in terms of a dynamic thermodynamic resolution mechanism.

AB - The title reaction is shown to afford the corresponding 1,2-diol monomethyl ethers in moderate-to-high levels of % ee (up to 98%) and % de (up to 90% anti), depending markedly on the aldehyde reactivity. The origin of the enantioselectivity is discussed in terms of a dynamic thermodynamic resolution mechanism.

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U2 - 10.1016/S0040-4039(99)01365-9

DO - 10.1016/S0040-4039(99)01365-9

M3 - Article

AN - SCOPUS:0033543757

SN - 0040-4039

VL - 40

SP - 6813

EP - 6816

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Enantioselective reactions of α-methoxybenzyllithium generated by t-BuLi/chiral bis(oxazoline) complex with aldehydes

Abstract

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