Masochistic nucleophilic attack

Scheme 12.21 Synthesis of substituted 2-hydroxymethyl quinuclidin-5-ols. Masochistic nucleophilic attack on quinuclidinone helix.

Thus, the masochistic nucleophilic attack from the supposedly more hindered face is favored affording quinuclidinols with natural configuration at C5. The right-handed helicity is conserved during preferred nucleophilic addition from the endo face the fully eclipsed high-energy C3v-like conformation is bypassed en route to the major products anti-82, anti-82, and anti-85. Stereochemical assignments at carbon C5 have been confirmed by NOE experiments and X-ray analyses of anti-85 and syn-85. 

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See also in sourсe #XX -- [ ]

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