References and Notes
<A NAME="RG20808ST-1">1</A>
Ouedraogo M.
Carreyre H.
Vandebrouck C.
Bescond J.
Raymond G.
Guissou I.-P.
Cognard C.
Becq F.
Potreau D.
Cousson A.
Marrot J.
Coustard J.-M.
J. Nat. Prod.
2007,
70:
2006
<A NAME="RG20808ST-2">2</A> The allyltitanium complex (S,S)-Ti-I was prepared according to:
Hafner A.
Duthaler RO.
Marti R.
Rihs G.
Rothe-Streit P.
Schwarzenbach F.
J.
Am. Chem. Soc.
1992,
114:
2321
The ee of 3 and
its S absolute configuration were determined by ¹H
NMR after derivatization with (S)- and
(R)-methoxyphenylacetic acids. See:
<A NAME="RG20808ST-3A">3a</A>
Dale JA.
Mosher
HS.
J.
Am. Chem. Soc.
1973,
95:
512
<A NAME="RG20808ST-3B">3b</A>
Trost BM.
Belletire JL.
Godleski S.
McDougal PG.
Balkovec
JM.
J. Org. Chem.
1986,
51:
2370
<A NAME="RG20808ST-3C">3c</A>
Seco JM.
Quiňoà E.
Riguera R.
Tetrahedron: Asymmetry
2001,
12:
2915
<A NAME="RG20808ST-4">4</A>
Evans DA.
Gauchet-Prunet JA.
J. Org. Chem.
1993,
58:
2446
<A NAME="RG20808ST-5">5</A>
Cossy J.
BouzBouz S.
Hoveyda AH.
J.
Organomet. Chem.
2001,
624:
327
<A NAME="RG20808ST-6">6</A>
Kingsbury JS.
Harrity JPA.
Bonitatebus PJ.
Hoveyda AH.
J.
Am. Chem. Soc.
1999,
121:
791
<A NAME="RG20808ST-7">7</A>
Still WC.
Gennari C.
Tetrahedron Lett.
1983,
24:
4405
<A NAME="RG20808ST-8">8</A>
Compound 9: R
f
= 0.23
(PE-EtOAc, 2:8); [α]
d
²0 +48.1
(c = 0.34, CHCl3) {Lit.
[¹]
[α]
d
²0 +40.2
(c = 0.40, CHCl3)}.
IR (neat): 3311, 2920, 1698, 1515 cm-¹. ¹H
NMR (400 MHz, CDCl3): δ = 7.05 (app
dt, J = 8.5, 2.5 Hz, 2 H), 6.88
(app dt, J = 9.5, 4.1 Hz, 1
H), 6.76 (app dt, J = 8.5, 2.5
Hz, 2 H), 6.02 (dt, J = 9.8,
1.9 Hz, 1 H), 5.32 (br s, 1 H), 4.65 (dddd, J = 7.7, 7.7,
7.7, 5.3 Hz, 1 H), 3.87 (m, 1 H), 2.67 (m, 2 H), 2.38 (m, 2 H),
2.00 (dt, J = 15.7, 8.2 Hz,
1 H), 1.90 (br s, 1 H, OH), 1.79 (m, 3 H). ¹³C
NMR (100 MHz, CDCl3): δ = 164.6 (s), 154.3
(s), 145.8 (d), 133.9 (s), 129.8 (2 × d), 121.5 (d), 115.7 (2 × d),
77.4 (d), 69.0(d), 42.4 (t), 39.7 (t), 31.2 (t), 29.8 (t). MS (EI,
70 eV): m/z (%) = 262
(5), 150 (2), 133 (10), 120 (9), 108 (27), 107 (100), 94 (14), 77
(49), 67 (23), 53 (22). HRMS (ESI): m/z [M + Na]+ calcd
for C15H18O4Na: 285.10987; found:
285.10973.
