Unusual Regioselectivity in the Reductive Coupling of Alkynes and Allenes by Hydrozirconation and Zinca‐Claisen Rearrangement | Zendy

Suzuki Keisuke | Zendy; Imai Takahiro | Zendy; Yamanoi Shigeo | Zendy; Chino Masao | Zendy; Matsumoto Takashi | Zendy

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Unusual Regioselectivity in the Reductive Coupling of Alkynes and Allenes by Hydrozirconation and Zinca‐Claisen Rearrangement

Author(s) -

Suzuki Keisuke,

Imai Takahiro,

Yamanoi Shigeo,

Chino Masao,

Matsumoto Takashi

Publication year - 1997

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199724691

Subject(s) - regioselectivity , chemistry , adduct , claisen rearrangement , zirconium , medicinal chemistry , stereochemistry , organic chemistry , catalysis

The α‐adduct is the sole product of the coupling of vinyl‐ and allylzirconium compounds with ZnCl 2 (see below), provided no Mg II salts are present. The zirconium compounds are formed in situ from alkynes and allenes, and the overall reaction opens a new preparative route to the vitamin E side chain through asymmetric induction in the 1,5‐position. R 1 = CH 2 OCPh 3 , R 2 = CHMeCH 2 OCH 2 OMe, “Zr” = [Cp 2 Zr(H)Cl].

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