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Please login to access the full content or check if you have access via8.1.26 Product Subclass 26: Bis(organosulfanyl)- and Bis(organoselanyl)methyllithium Compounds
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Nájera, C.; Yus, M., Science of Synthesis, (2006) 8, 813.
General Introduction
Organolithium compounds derived from formaldehyde or other aldehyde dithioacetals are important organometallic compounds in organic synthesis, especially useful as formyl or acyl anion equivalents (Scheme 1).[1–4] These umpoled reagents are prepared mainly by deprotonation of the corresponding dithio compounds with alkyllithium reagents in tetrahydrofuran at low temperature and, after reaction with electrophiles, the corresponding carbonyl functionality can be regenerated by using heavy metal coordination, alkylation, or oxidation.[5] The use of these acyllithium equivalents, especially the cyclic counterpart derived from 1,3-dithiane that presents the highest nucleophilicity among all these species, has become a classic method for the total synthesis of natural products.
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References
| [1] | Meeee, M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, e 888. |
| [2] | Meee, M. M., Me Meeeeee Meeeeeee, Meee, M. M., Me.; Meeee: Mee Meee, (8888); e 88. |
| [3] | Meeeée, M.; Meeeee, M., Me Meeeeeeeeeeee Meeeeee Meeeeeeeee Meeee Meeeeeeeeeeeeee, Meeeeeeee, M. M.; Meee-Meee, M.; Meee, M. M., Mee.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
| [4] | Meöeee, M.-M.; Meeeeee, M., Meeeeeeee, (8888), 888. |
| [5] | Meeeee, M. M.; Meee, M. M. M., Meeeeeeeee Meeeee ee Meeeeee Meeeeeeee, 8ee ee.; Meeee: Mee Meee, (8888); e 888. |
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- 8.Meeeee-Meee, (8888) M 88e, 888.
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