Synthesis, stereostructure, and conformations of novel Bi- and trifunctional (+)-isomenthone derivatives

被引：4

作者：

Gardiner, JM

Crewe, PD

Smith, GE

Veal, KT

Pritchard, RG

Warren, JE

机构：

[1] UMIST, Dept Chem, Manchester M60 1QD, Lancs, England

[2] GlaxoSmithKline, Harlow CM19 5AW, Essex, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 04期

关键词：

D O I：

10.1021/ol027434e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Following protection, keto alcohols 4 [from (+)-isomenthone] undergo reduction to 1,3-diol 6 (S configuration at the new stereocenter). Organometallic C-nucleophiles add to the carbonyl with the same facial selectivity as hydride, providing multifunctional derivatives, e.g., 8 and 9, with five contiguous stereocenters. The side chain hydroxyl of 4 is elaborated into amino and amide derivatives (e.g., 12). Structural analysis shows that 6, 8, 9, and the precursor to 12 (10) all adopt triaxial solid-state conformations.

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页码：467 / 470

页数：4

相关论文

共 23 条

[1]

[Anonymous], COMPREHENSIVE ASYMME

[2] THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES [J].

BLASER, HU .

CHEMICAL REVIEWS, 1992, 92 (05) :935-952

[3] New homochiral ketoalcohols from aldol reactions of (+)-isomenthone and reversal of diastereoselectivity [J].

Chughtai, JH ;

Gardiner, JM ;

Harris, SG ;

Parsons, S ;

Rankin, DWH ;

Schwalbe, CH .

TETRAHEDRON LETTERS, 1997, 38 (52) :9043-9046

[4] Atropisomeric amides as chiral ligands: Using (-)-sparteine-directed enantioselective silylation to control the conformation of a stereogenic axis [J].

Clayden, J ;

Johnson, P ;

Pink, JH ;

Helliwell, M .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) :7033-7040

[5] Chiral β- and γ-aminoalcohols derived from (+)-camphor and (-)-fenchone as catalysts for the enantioselective addition of diethylzinc to benzaldehyde [J].

Dimitrov, V ;

Dobrikov, G ;

Genov, M .

TETRAHEDRON-ASYMMETRY, 2001, 12 (09) :1323-1329

[6] Synthesis and proof of stereostructure of a new (+)-isomenthone-derived homochiral 1,3-diol [J].

Gardiner, JM ;

Chughtai, JH ;

Sadler, IH .

TETRAHEDRON-ASYMMETRY, 1998, 9 (04) :599-606

[7]

GARDINER JM, 2002, UNPUB

[8]

GARDINER JM, UNPUB

[9] Kinetic resolution in palladium-catalyzed asymmetric allylic alkylations by a P,O ligand system [J].

Gilbertson, SR ;

Lan, P .

ORGANIC LETTERS, 2001, 3 (14) :2237-2240

[10] Chiral molybdenum(VI) and tungsten(VI) 2′-pyridinyl alcoholate complexes.: Synthesis, structure and catalytic properties in asymmetric olefin epoxidation [J].

Herrmann, WA ;

Haider, JJ ;

Fridgen, J ;

Lobmaier, GM ;

Spiegler, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 603 (01) :69-79