Toward the development of a general chiral auxiliary 2. Evaluation of camphor lactam imide auxiliaries for asymmetric aldol reactions

Some Synthetic Uses of Double‐Bonded Functional Groups

“…A camphor lactam imide auxiliary has also been used in a similar fashion (equation 124) 501 . Using this type of protocol, but replacing the aldehyde with an imine, the docetaxel (an important anticancer compound related to taxol) side chain has been prepared in 66% yield and 99% ee, as shown in equation 125 502 .…”

The Development of a Convergent and Efficient Enantioselective Synthesis of the Bengamides via a Common Polyol Intermediate

“…Calculations of possible transition-state structures employing low-order semi-empirical molecularorbital theory were consistant with the observed stereochemical outcome. The lowestenergy transition-state structure had the BÀO bond of the enolate anti to that of the lactam CO group, thereby minimizing dipole interactions, with subsequent approach of the aldehyde to the sterically less-encumbered face of the enolate, i.e., syn to the CH 2 bridge, affording the (2S,3R)-diastereoisomer in very high stereoselectivity [13] [17]. The steric bulk and rigidity of the camphor-derived auxiliary 8 and the aforementioned dipole/dipole interactions result in a highly organized transition state with excellent control over bond-rotamer populations.…”