Cryptochirality in stereochemistry is a special case of chirality where due to the electronic properties of the chiral molecule its specific rotation is non-measurable. The term was introduced by K. Mislow in 1977.
It is still possible to distinguish between the two enantiomers by asymmetric synthesis with the (S)-alkane 3 in an autocatalytic system of the achiral aldehyde 1 and achiral diisopropylzinc 2 to the chiral (R)-alcohol 4 with enantiomeric excess 94%:
For chiral induction to be possible C-H bonds in the alkane are believed to interact with the pi electrons of the aldehyde.
- More on diisopropylzinc autocatalysis see: homochirality
- Chiral Discrimination of Cryptochiral Saturated Quaternary and Tertiary Hydrocarbons by Asymmetric Autocatalysis Kawasaki, T.; Tanaka, H.; Tsutsumi, T.; Kasahara, T.; Sato, I.; Soai, K. J. Am. Chem. Soc.; (Communication); 2006; 128(18); 6032-6033. Abstract
- Cryptochirality and dendrimers Struijk, MP Peerlings, HWI Meijer, EW Polymer Preprints 37(2), 497-498 (1996) Article