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Breit, B., Science of Synthesis, (2007) 25, 295.
The rigid skeleton of bicyclic monoterpenes allows for synthetically useful levels of diastereoselectivity. Thus, hydroformylation of β-pinene (51) with triphenylphosphine- or triphenyl phosphite modified rhodium catalysts gives the linear aldehyde 52 in good yield and selectivity (Scheme 18).[80] Aldehyde 53 and α-pinene (54) are minor products.
Meeeee 88 Meeeeeeeeeeeeee Meeeeeeeeeeeeeee ee (−)-β-Meeeee[88]
M | Meeee (M/Me) | Meeeeeee (MMe) | Meeee (88/88/88) | Meeeeeeeee (%) | Mee |
---|---|---|---|---|---|
MMe8 | 8.8 | 8.8 | 88:8:8 | 88 | [88] |
M(MMe)8 | 8 | 8.8 | 88:8:8 | 88 | [88] |
(8-e-MeM8M8-M)8M | 8.8 | 8.8 | 8:8:8 | 88 | [88] |
M eeee eeeeeeeee eeeeeeeee ee eee eeeeeeeeeeeeeeee ee α-eeeeee (88), eeeee eee eeeeeeeeeeeeee eeeeee ee eeeeee eeeeeeeee eeeeee eeeeeeeeeeeeeeee. Meeeeee, eeeeeeeee eeeeeeeeeee 88 (eee Meeeee 88, Meeeeee 88.8.88.8) ee e eeeeeeee eeeeeee eeeeeeee, eeeeeeeeeeeeeeee ee 88 eeeeee eeeeeeee ee eeeee eeeeeeee 88 (88% eeeeeeeeee) ee eeee eeeee-, eeeee-, eee eeeeeeeeeeeeeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeeeeeeeee Meeeeeeeeeeeeeee ee (−)-α-Meeeee[88]
Meeee eeee eeeeeee eeeeeeeeee, eeeeeeeeeeeeeee eeeeeeeeeeeeeeee ee eee eeeeeeeee eeeeeee eeeeeee 88 eee ee eeeeeeee ee eeee eee α-eeeeee eeeeeeeeee 88 ee eeee eeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeeeeeeeee Meeeeeeeeeeeeeee ee e Meeeeeeee Meeeee Meeeeee Meeeeee[88]
References
[66] | Meeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meeee, M., Meee.–Mee. M., (8888) 8, 8888. |
[80] | Meeee, M.; Meeee, M., Mee M. Meee., (8888) 88, 8888. |
[81] | Möeöe, M.; Méeee-Méeee, M.; Meee, M.; Meeó, M.; Meee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.