130715-22-9Relevant academic research and scientific papers
DIASTEREOSELECTIVE MANIPULATIONS OF CONFORMATIONALLY RESTRICTED ENANTIOMERICALLY PURE BICYCLOALKANES. 1. NUCLEOPHILIC ADDITIONS TO THE CARBONYL CARBONS OF BICYCLOALKAN-2-ONES
Mash, Eugene A.,Kaczynski, Michelle A.,Dolata, Daniel P.
, p. 4565 - 4568 (1990)
Additions of nucleophiles to the carbonyls of several enantiomerically pure bicycloalkan-2-ones were found to be highly diastereoselective.
Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 2. Nucleophilic additions to the carbonyl carbons of bicyclot[m.1.0]alkan-2-ones
Mash, Eugene A.,Gregg, Timothy M.,Kaczynski, Michelle A.
, p. 2743 - 2752 (2007/10/03)
Enantiomerically enriched bicyclo[m.1.0]alkan-2-ones having larger ring sizes between five and 16 members were prepared and subjected to additions of nucleophiles to the carbonyl carbon. Such additions were efficient and highly diastereoselective for all nucleophiles for bicycles with ring sizes greater than seven. Diastereoselectivity for these additions is rationalized by assuming early transition states and exposure of the same carbonyl face to the ring exterior in the vast majority of populated conformers for each bicyclic ketone.
