Intramolecular Allylsilane Addition to Chiral Alkylidene‐1,3‐dicarbonyl Compounds for the Synthesis of Enantiomerically Pure  trans ‐1,2‐Disubstituted Cyclopentanes and Cyclohexanes | Zendy

Tietze Lutz F. | Zendy; Schünke Christian | Zendy

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Intramolecular Allylsilane Addition to Chiral Alkylidene‐1,3‐dicarbonyl Compounds for the Synthesis of Enantiomerically Pure trans ‐1,2‐Disubstituted Cyclopentanes and Cyclohexanes

Author(s) -

Tietze Lutz F.,

Schünke Christian

Publication year - 1995

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.199517311

Subject(s) - cyclopentanes , cyclohexanes , stereocenter , chemistry , lewis acids and bases , stereochemistry , organic chemistry , enantioselective synthesis , catalysis

Three new stereogenic centers characterize the 1,2‐ trans ‐disubstituted cyclopentanes 2a and cyclohexanes 2b , which can be prepared enantiomerically pure with the Lewis acid SnCl 4 in a highly selective SnCl 4 ‐induced cyclization of the chiral alkylidene malonic acid derivatives 1a and 1b , respectively. The chiral auxiliary can be removed from 2 with LiAlH 4 .

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