Reviews, Commentaries, etc. - Arai, Midori

Enantioselective synthesis of alpha-methylene-gamma-butyrolactones using chiral Pd(II)-SPRIX catalyst

C Muthiah, MA Arai, T Shinohara, T Arai, S Takizawa, H Sasai

TETRAHEDRON LETTERS (PERGAMON-ELSEVIER SCIENCE LTD)  44 ( 28 ) 5201 - 5204 2003.07

ISSN  0040-4039

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Combination of Pd(OCOCF3)(2) and (M,S,S)-iPr-SPRIX ligand promoted the intramolecular cyclization of 2-alkynoates very effectively to form alpha-methylene-gamma-butyrolactones in good yields with up to 92% ee. (C) 2003 Elsevier Science Ltd. All rights reserved.

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Synthesis and character of new bis(isoxazoline) ligands

T Shinohara, K Wakita, MA Arai, T Arai, H Sasai

HETEROCYCLES (PERGAMON-ELSEVIER SCIENCE LTD)  59 ( 2 ) 587 - 593 2003.03

ISSN  0385-5414

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Synthesis of two kinds of new bis(isoxazoline) ligand, achiral 2,2'-bis(isoxazolinyl)propane and (R)-2,2'-bis(isoxazolinyl)-1,1'-binaphthyl bearing an axial chirality is described. Both of the bis(isoxazoline) ligands accelerated the Pd(II)-catalyzed Wacker-type cyclization of alkenyl alcohol. The isoxazoline ligands were found to be essential to promote the cyclization.

Synthesis of new chiral bis(isoxazoline) ligands containing spiro[5.5]undecane skeleton

MA Arai, M Kuraishi, T Arai, H Sasai

CHIRALITY (WILEY-LISS)  15 ( 1 ) 101 - 104 2003.01

ISSN  0899-0042

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New chiral bis(isoxazoline) ligands bearing a spiro[5.5]undecane skeleton were designed and synthesized in five steps from diethyl malonate (3). These ligands showed a coordinating ability to Cu(II) as chiral ligands. A complex of (+)-(M*,S*,R*)-[5.5]-SPRDC 2b and Cu(OTf)(2) catalyzed the conjugate addition of diethylzine to 2-cyclohexenone (8) to give (S)-3-ethyl-cyclohexanone (9) in 93% yield with 54% ee. (C) 2002 Wiley-Liss, Inc.

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The first enantioselective intramolecular aminocarbonylation of alkenes promoted by Pd(II)-spiro bis(isoxazoline) catalyst

T Shinohara, MA Arai, K Wakita, T Arai, H Sasai

TETRAHEDRON LETTERS (PERGAMON-ELSEVIER SCIENCE LTD)  44 ( 4 ) 711 - 714 2003.01

ISSN  0040-4039

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The highly ligand acceleration effect of spiro bis(isoxazoline) ligand (SPRIX) on the Pd(II)-catalyzed intramolecular aminocarbonylation of alkenyl amine derivatives was realized. Furthermore, the chiral Pd(II)-SPRIX catalyst accomplished the first enantioselective intramolecular aminocarbonylation. The reaction of N-(2,2-dimethyl-pent-4-enyl)-p-toluenesulfonamide in the presence of Pd(II)-SPRIX catalyst and p-benzoquinone in methanol under a carbon monoxide atmosphere afforded [4,4-dimethyl-1-(p-toluene-sulfonyl)-pyrrolidin-2-yl]-acetic acid methyl ester in good yield with moderate enantioselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.

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Development of the first spiro bis (isoxazoline) ligands (SPRIXs)

My Favorite Organic Synthesis The Society of Synthetic Organic Chemistry, Japan Ed. pp 176-177 2002

Development of the first spiro bis (isoxazoline) ligands (SPRIXs)

Latest Frontiers of Organic Synthesis, ed. Yuichi Kobayashi, Research Signpot 49-64 2002

A new asymmetric Wacker-type cyclization and tandem cyclization promoted by Pd(II)-spiro bis(isoxazoline) catalyst

MA Arai, M Kuraishi, T Arai, H Sasai

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (AMER CHEMICAL SOC)  123 ( 12 ) 2907 - 2908 2001.03

ISSN  0002-7863

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Design and synthesis of the first spiro bis(isoxazoline) derivatives as asymmetric ligands

MA Arai, T Arai, H Sasai

ORGANIC LETTERS (AMER CHEMICAL SOC)  1 ( 11 ) 1795 - 1797 1999.12

ISSN  1523-7060

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[GRAPHICS]A chiral bis(isoxazoline) ligand (SPRIX) containing a rigid spiro skeleton was designed and synthesized via a double intramolecular nitrile oxide cycloaddition, The optically pure SPRIX greatly accelerated the Cu(acac)(2)-catalyzed asymmetric reaction of diisopropylzinc with cyclohexenone to give the Michael adduct with 49% ee. This is the first example of the use of an isoxazoline ligand for a transition metal catalyzed reaction. The X-ray crystallographic analysis of the hexacoordinated copper complex of SPRIX confirmed the ligand character.

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The first chiral spiro bis(isoxazoline) ligands.

MA Arai, T Arai, H Sasai

ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY (AMER CHEMICAL SOC)  217   U173 - U173 1999.03

ISSN  0065-7727

Rational design, synthesis, and evaluation of a new type of PKC inhibitor

M Sodeoka, MA Arai, K Adachi, K Uotsu, M Shibasaki

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (AMER CHEMICAL SOC)  120 ( 2 ) 457 - 458 1998.01

ISSN  0002-7863

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Asymmetric Heck reaction-carbanion capture process. Catalytic asymmetric total synthesis of (-)-Delta(9(12))-capnellene

T Ohshima, K Kagechika, M Adachi, M Sodeoka, M Shibasaki

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (AMER CHEMICAL SOC)  118 ( 30 ) 7108 - 7116 1996.07

ISSN  0002-7863

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An asymmetric Heck reaction-carbanion capture process was realized for the first time, making possible the catalytic asymmetric synthesis of various functionalized bicyclo[3.3.0]octane derivatives 6 in up to 94% ee. Sodium bromide had interesting effects on this asymmetric Heck reaction-carbanion capture process, and these effects were useful for improving the enantiomeric excess. Furthermore, the catalytic asymmetric synthesis of (-)-Delta(9(12))-capnellene (7) was achieved for the first time, using 6b as a key intermediate and a radical cyclization as a key step.

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