Abstract
An efficient asymmetric synthesis of bicyclo[3.1.0]hexane derivatives was achieved. The three-step conversion of 6-hydroxytricyclo[3.2.1.02,7]octan-3-one 2, (derived from 3-oxatricyclo[3.3.1.02,4]nonan-7-one 1 through an asymmetric deprotonation reaction) led to 6 in optically active form. Alternatively, the asymmetric deprotonation reaction of meso-cyclic ketones 9a and 9b with several chiral lithium amide bases was examined to give silyl enol ether 12 and triflate 21 with high enantioselectivity. The absolute configuration of the triflate 21 was determined by investigation of the chemical relationship between 21 and 6.
| Original language | English |
|---|---|
| Pages (from-to) | 1519-1527 |
| Number of pages | 9 |
| Journal | Tetrahedron Asymmetry |
| Volume | 13 |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - Aug 1 2002 |
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ASJC Scopus subject areas
- Inorganic Chemistry
- Organic Chemistry
- Materials Chemistry
- Drug Discovery
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Enantioselective construction of bicyclo[3.1.0]hexane derivatives through asymmetric deprotonation of meso-cyclic ketones. / Abe, Hitoshi; Tsujino, Takenori; Araki, Kenta; Takeuchi, Yasuo; Harayama, Takashi.
In: Tetrahedron Asymmetry, Vol. 13, No. 14, 01.08.2002, p. 1519-1527.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Enantioselective construction of bicyclo[3.1.0]hexane derivatives through asymmetric deprotonation of meso-cyclic ketones
AU - Abe, Hitoshi
AU - Tsujino, Takenori
AU - Araki, Kenta
AU - Takeuchi, Yasuo
AU - Harayama, Takashi
PY - 2002/8/1
Y1 - 2002/8/1
N2 - An efficient asymmetric synthesis of bicyclo[3.1.0]hexane derivatives was achieved. The three-step conversion of 6-hydroxytricyclo[3.2.1.02,7]octan-3-one 2, (derived from 3-oxatricyclo[3.3.1.02,4]nonan-7-one 1 through an asymmetric deprotonation reaction) led to 6 in optically active form. Alternatively, the asymmetric deprotonation reaction of meso-cyclic ketones 9a and 9b with several chiral lithium amide bases was examined to give silyl enol ether 12 and triflate 21 with high enantioselectivity. The absolute configuration of the triflate 21 was determined by investigation of the chemical relationship between 21 and 6.
AB - An efficient asymmetric synthesis of bicyclo[3.1.0]hexane derivatives was achieved. The three-step conversion of 6-hydroxytricyclo[3.2.1.02,7]octan-3-one 2, (derived from 3-oxatricyclo[3.3.1.02,4]nonan-7-one 1 through an asymmetric deprotonation reaction) led to 6 in optically active form. Alternatively, the asymmetric deprotonation reaction of meso-cyclic ketones 9a and 9b with several chiral lithium amide bases was examined to give silyl enol ether 12 and triflate 21 with high enantioselectivity. The absolute configuration of the triflate 21 was determined by investigation of the chemical relationship between 21 and 6.
UR - http://www.scopus.com/inward/record.url?scp=0036674123&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036674123&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(02)00405-6
DO - 10.1016/S0957-4166(02)00405-6
M3 - Article
AN - SCOPUS:0036674123
VL - 13
SP - 1519
EP - 1527
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 14
ER -