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Protolytic Opening of Two Diastereoisomeric Cyclopropanols
Author(s) -
Schönholzer Peter,
Wan Terence S.,
Fischli Albert
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670307
Subject(s) - chemistry , inversion (geology) , ring (chemistry) , walden inversion , medicinal chemistry , organic chemistry , geology , paleontology , structural basin
Abstract Cob(I) alamin ( 1(I) )‐catalyzed reduction of the aldehyde 2 led to the two crystalline cyclopropanols 3 and 4 (see Scheme 2 ). The protolytic ring‐opening starting from 3 produced the saturated aldehydes 6 and 7;8 was formed in traces only (see Scheme 3 ). The protolysis starting from 3 led, therefore, mainly to retention of configuration at the spiro C‐atom ( 7 ); ring‐opening with inversion was observed in traces only ( 8 ). Starting from 4 , the protolysis produced 9 and 7 ; the absence of 8 showed this protolysis to proceed 9 and 7 ; the absence of 8 showed this protolysis to proceed exclusively with inversion of configuration at the spiro center. Of the p ‐bromobenzoate 5 ( cf. Scheme 2 ) the structure has been determined by X‐ray analysis.