External chiral ligand-induced enantioselective lithiation/S(E)2 reactions of isochroman and phthalan

K. Tomooka; L. F. Wang; F. Okazaki; T. Nakai

doi:10.1016/S0040-4039(00)01028-5

External chiral ligand-induced enantioselective lithiation/S(E)2 reactions of isochroman and phthalan

K. Tomooka, L. F. Wang, F. Okazaki, T. Nakai

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

51 Citations (Scopus)

Abstract

Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO₂ is shown to afford the α-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetric induction is proved to occur at the post-lithiation step. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	6121-6125
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4039(00)01028-5
Publication status	Published - Aug 5 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)01028-5

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title = "External chiral ligand-induced enantioselective lithiation/S(E)2 reactions of isochroman and phthalan",

abstract = "Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO2 is shown to afford the α-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetric induction is proved to occur at the post-lithiation step. (C) 2000 Elsevier Science Ltd.",

author = "K. Tomooka and Wang, {L. F.} and F. Okazaki and T. Nakai",

note = "Funding Information: This work was supported by the JSPS Research for the Future Program.",

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doi = "10.1016/S0040-4039(00)01028-5",

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TY - JOUR

T1 - External chiral ligand-induced enantioselective lithiation/S(E)2 reactions of isochroman and phthalan

AU - Tomooka, K.

AU - Wang, L. F.

AU - Okazaki, F.

AU - Nakai, T.

N1 - Funding Information: This work was supported by the JSPS Research for the Future Program.

PY - 2000/8/5

Y1 - 2000/8/5

N2 - Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO2 is shown to afford the α-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetric induction is proved to occur at the post-lithiation step. (C) 2000 Elsevier Science Ltd.

AB - Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO2 is shown to afford the α-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetric induction is proved to occur at the post-lithiation step. (C) 2000 Elsevier Science Ltd.

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U2 - 10.1016/S0040-4039(00)01028-5

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SN - 0040-4039

VL - 41

SP - 6121

EP - 6125

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

External chiral ligand-induced enantioselective lithiation/S(E)2 reactions of isochroman and phthalan

Abstract

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