Highly enantioselective homogeneous catalysis of chiral rare earth phosphates in the hetero-Diels-Alder reaction

Hiroshi Furuno; Takeshi Kambara; Yumiko Tanaka; Takeshi Hanamoto; Takumi Kagawa; Junji Inanaga

doi:10.1016/S0040-4039(03)01460-6

Highly enantioselective homogeneous catalysis of chiral rare earth phosphates in the hetero-Diels-Alder reaction

Hiroshi Furuno, Takeshi Kambara, Yumiko Tanaka, Takeshi Hanamoto, Takumi Kagawa, Junji Inanaga

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

57 Citations (Scopus)

Abstract

Two types of novel rare earth (RE) complexes were synthesized and used as a chiral Lewis acid catalyst for the hetero-Diels-Alder reaction of carbonyl compounds with the Danishefsky's diene under homogeneous conditions. The Y[(R)-H₈-BNP]₃ (3-Y)-catalyzed reaction of aromatic aldehydes and the Yb[(R)-BNP]₃ (1-Yb)-catalyzed reaction of phenylglyoxylates afforded the corresponding cycloadducts with excellent optical purities (up to 99% ee) in high yields at room temperature. The successful recycling uses of the scandium catalyst (3-Sc) are also described.

Original language	English
Pages (from-to)	6129-6132
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4039(03)01460-6
Publication status	Published - Aug 4 2003

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(03)01460-6

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title = "Highly enantioselective homogeneous catalysis of chiral rare earth phosphates in the hetero-Diels-Alder reaction",

abstract = "Two types of novel rare earth (RE) complexes were synthesized and used as a chiral Lewis acid catalyst for the hetero-Diels-Alder reaction of carbonyl compounds with the Danishefsky's diene under homogeneous conditions. The Y[(R)-H8-BNP]3 (3-Y)-catalyzed reaction of aromatic aldehydes and the Yb[(R)-BNP]3 (1-Yb)-catalyzed reaction of phenylglyoxylates afforded the corresponding cycloadducts with excellent optical purities (up to 99% ee) in high yields at room temperature. The successful recycling uses of the scandium catalyst (3-Sc) are also described.",

author = "Hiroshi Furuno and Takeshi Kambara and Yumiko Tanaka and Takeshi Hanamoto and Takumi Kagawa and Junji Inanaga",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Culture, Sports, Science and Technology, Japan, the Japan Society for the Promotion of Science, and also by the Kyushu University P&P Programs {\textquoteleft}Green Chemistry{\textquoteright} (to J.I.).",

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doi = "10.1016/S0040-4039(03)01460-6",

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TY - JOUR

T1 - Highly enantioselective homogeneous catalysis of chiral rare earth phosphates in the hetero-Diels-Alder reaction

AU - Furuno, Hiroshi

AU - Kambara, Takeshi

AU - Tanaka, Yumiko

AU - Hanamoto, Takeshi

AU - Kagawa, Takumi

AU - Inanaga, Junji

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Culture, Sports, Science and Technology, Japan, the Japan Society for the Promotion of Science, and also by the Kyushu University P&P Programs ‘Green Chemistry’ (to J.I.).

PY - 2003/8/4

Y1 - 2003/8/4

N2 - Two types of novel rare earth (RE) complexes were synthesized and used as a chiral Lewis acid catalyst for the hetero-Diels-Alder reaction of carbonyl compounds with the Danishefsky's diene under homogeneous conditions. The Y[(R)-H8-BNP]3 (3-Y)-catalyzed reaction of aromatic aldehydes and the Yb[(R)-BNP]3 (1-Yb)-catalyzed reaction of phenylglyoxylates afforded the corresponding cycloadducts with excellent optical purities (up to 99% ee) in high yields at room temperature. The successful recycling uses of the scandium catalyst (3-Sc) are also described.

AB - Two types of novel rare earth (RE) complexes were synthesized and used as a chiral Lewis acid catalyst for the hetero-Diels-Alder reaction of carbonyl compounds with the Danishefsky's diene under homogeneous conditions. The Y[(R)-H8-BNP]3 (3-Y)-catalyzed reaction of aromatic aldehydes and the Yb[(R)-BNP]3 (1-Yb)-catalyzed reaction of phenylglyoxylates afforded the corresponding cycloadducts with excellent optical purities (up to 99% ee) in high yields at room temperature. The successful recycling uses of the scandium catalyst (3-Sc) are also described.

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U2 - 10.1016/S0040-4039(03)01460-6

DO - 10.1016/S0040-4039(03)01460-6

M3 - Article

AN - SCOPUS:0037629594

SN - 0040-4039

VL - 44

SP - 6129

EP - 6132

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Highly enantioselective homogeneous catalysis of chiral rare earth phosphates in the hetero-Diels-Alder reaction

Abstract

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