32.2. 6 Monofunctionalized Allenes (Update 2018)
Book
Editors: Brøndsted Nielsen, M.; Krause, N.; Rademann, J.; Ramsden, C. A.; Reissig, H.-U.
Title: Knowledge Updates 2018/1
Print ISBN: 9783132423138; Online ISBN: 9783132423169; Book DOI: 10.1055/b-005-145253
1st edition © 2018 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Koch, G.; Molander, G. A.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract

This chapter is an update to Science of Synthesis Section 32.2, covering the synthesis of allenes bearing one heteroatom substituent on the cumulated diene core. It covers the literature from 2008 to 2016. Many routes to these allenes start from alkynes, enynes, or propargylic systems and the syntheses proceed through substitution/rearrangement, but reactions involving the modification of an existing allene core are also included. In recent years, the synthesis of enantiomerically pure allenes has been of particular interest.
Key words
allenes - haloallenes - allenyl ethers - allenyl sulfides - allenylamides - allenylamines - allenylphosphorus compounds - allenylsilanes - rearrangement - isomerization - alkynes - enynes - propargylic systems- 11 Braddock DC, Bhuva R, Pérez-Fuertes Y, Pouwer R, Roberts CA, Ruggiero A, Stokes ESE, White AJP. Chem. Commun. (Cambridge) 2008; 44: 1419
- 15 Tap A, Lecourt C, Dhambri S, Arnould M, Galvani G, Nguyen Van Buu O, Jouanneau M, Férézou J.-P, Ardisson J, Lannou M.-I, Sorin G. Chem.–Eur. J. 2016; 22: 4938
- 18 Moreno-Clavijo E, Carmona AT, Reissig H.-U, Moreno-Vargas AJ, Alvarez E, Robina I. Org. Lett. 2009; 11: 4778
- 23 Kawamura T, Inagaki F, Narita S, Takahashi Y, Hirata S, Kitagaki S, Mukai C. Chem.–Eur. J. 2010; 16: 5173
- 26 Potapov VA, Panov VA, Musalov MV, Musalova MV, Amosova SV. Russ. J. Org. Chem. (Engl. Transl.) 2016; 52: 1054
- 27 Levanova EP, Grabel’nykh VA, Vakhrina VS, Russavskaya NV, Albanov AI, Rozentsveig IB, Korchevin NA. Russ. J. Gen. Chem. (Engl. Transl.) 2014; 84: 439
- 28 Rozentsveig IB, Nikonova VS, Levanova EP, Korchevin NA. Russ. J. Org. Chem. (Engl. Transl.) 2016; 52: 1264