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25.1.11.4.1 Variation 1: Cyclic Alkenes

DOI: 10.1055/sos-SD-025-00196

Breit, B.Science of Synthesis, (200725295.

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.

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Meeeeeeeeee 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]

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References