Steric Course of the Reduction of Ketoacetal Esters with Alkali Metals in Liquid Ammonia | Zendy

Jaisli Fritz | Zendy; Sternbach Daniel | Zendy; Eschenmoser Albert | Zendy; Shibuya Masayuki | Zendy

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Steric Course of the Reduction of Ketoacetal Esters with Alkali Metals in Liquid Ammonia

Author(s) -

Jaisli Fritz,

Sternbach Daniel,

Eschenmoser Albert,

Shibuya Masayuki

Publication year - 1979

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.197906371

Subject(s) - alkali metal , steric effects , alkoxide , chemistry , bridge (graph theory) , ammonia , liquid ammonia , inorganic chemistry , oxygen , reduction (mathematics) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , mathematics , medicine , geometry

The stereochemistry of the reduction of keto groups such as in (1) by alkali metals is influenced by neighboring oxygen functions. Compounds (1) . R 1 , R 2 H, CO 2 Me, give (2) and (3) in th ratio 1:2.5–3. This unexpected finding is explained in terms of stabilization of the axial alkoxide corresponding to (3) by a Li bridge. Na + and K + are too large for bridge formation; they give mainly (2) .

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